Supramolecular complexes of carbon nanohoops with fullerenes play a key role for the design of novel nanomaterials with technological applications. Herein we investigate with density functional theory (DFT) methods the capability of neutral and dioxidized cycloparaphenylenes (CPPs) to encapsulate all-boron fullerene B₄₀. Our results show that [9]CPP and [10]CPP are feasible host candidates to encapsulate B₄₀ displaying comparable complexation energies with the all-carbon analog [10]CPP⊃C₆₀. Upon dioxidation the host-guest interactions are not affected, whereas the positive charge is delocalized on the CPPs leading to global aromatic character of the hosts. Consequently, the dicationic complexes [n]CPP²⁺⊃B₄₀ and [10]CPP²⁺⊃C₆₀display augmented global shielding cones that strongly shield the guests, as manifested by large upfield shifts in ¹¹B-NMR and ¹³C-NMR signals. Hence, CPP complexes with carbon fullerenes can be extended borospherene B₄₀ host-guest complexes, as well as to doubly oxidized species stabilized by global host aromaticity, expanding our understanding of carbon nanohoop complexes to boron-based fullerenes.

Lingas R., Charistos* N. D., Muñoz-Castro* A.

Charge Delocalization and Aromaticity of Doubly Reduced Double-walled Carbon Nanohoops

Physical Chemistry Chemical Physics 2023, 25 , 19481-19491, DOI: 10.1039/D3CP01994B 2023 PCCP HOT Article

Cycloparaphenylenes (CPPs) exhibit selective host capabilities, featuring the ability to incorporate smaller CPPs to form double-walled host-guest complexes. Moreover, CPPs can also be stabilized by global aromaticity under twofold oxidation or reduction, involving an electronic conjugation along with the overall structural backbone. Herein we explore the structural modifications, bonding, electron delocalization and magnetic properties of doubly reduced double-walled CPP complexes with DFT methods, in the isolated and aggregate [n+5]CPP>[n]CPP2- (n = 5-8) species. Our results show that the hosts undergo structural, bonding and delocalization deformations towards quinoidal configurations and exhibit global long-ranged shielding cones similar to global aromatic free dianionic CPPs, accounting for a charge delocalization on the outer nanohoops, whereas the guests preserve local aromatic benzenoid configurations, resulting in global and local aromatic circuits within the host-guest aggregate. This observation suggests that in multi-layered related species electronic delocalization will be retained at the outer structural surface. The aromaticity of the hosts is manifested in the strong upfield shifts of 1H-NMR signals of the guests. Hence, CPP complexes can be extended to doubly reduced species stabilized by global host aromaticity expanding our understanding of doubled-walled nanotubes at the nanoscaled regime.

Lingas R., Charistos* N. D., Muñoz-Castro* A.

Local and Global Aromaticity under Rotation. Analysis of Two- and Three-Dimensional Representative Carbon Nanostructures

Physical Chemistry Chemical Physics 2023, 25 , 14285-14293, DOI: 10.1039/D3CP00569K

Nanoscaled 2D and 3D carbon structures with closed curved π-surfaces are of relevance in the development of desirable building units for material science. Such species are able to sustain local and global aromatic circuits involving isolated regions or the overall structural backbone, respectively. Here we account for local and global aromaticity under rotation of representative two- and three-dimensional species involving para-connected and fused edge-sharing phenyl rings ([8]CPP, [10]CPP, CNB), and C60 fullerene at different charge states. Our results denote that nanoscaled 2D global aromatics mimic the behaviour of the most prototypical aromatic 6π-circuit, given by benzene, where the shielding cone property varies along the rotation motion. In contrast, 3D spherical aromatics remain almost invariant under rotation, given the distinctive characteristics of such species, differing from 2D global aromatics. Under rotation, the variation of the anisotropic effect inherent to such nanoscaled structures is accounted for, which is relevant to rationalize variation in NMR signal shifts upon the formation of host-guest aggregates.

Lingas R., Charistos* N. D., Muñoz-Castro* A.

Aromaticity of ortho and meta 8-cycloparaphenylene and their dications: Induced magnetic field analysis with localized and delocalized orbitals in strained nanohoops

ChemPhysChem 2021, 22 (8) , 741-751 , DOI: 10.1002/cphc.202100057

Dications of cycloparaphenyles ([n]CPPs) are known to exhibit in-plane global aromaticity, contained in a nanobelt structure. Recently synthesized ortho and meta isomers of [n]CPPs break the radial symmetry of π structure incorporating perpendicular oriented π orbitals. Herein we set to explore the aromaticity of neutral and dicationic ortho and meta isomers of [8]CPP by dissecting the induced magnetic field to contributions of the twofold radial/perpendicular π system using delocalized canonical molecular orbitals (CMO), and introducing the natural localized molecular orbitals (NLMO) analysis with DFT methods. The dications sustain a reduced global aromatic character of the radial π system under a perpendicular orientation of the external field which declines from ortho¬ to meta isomer and reinforces local aromaticity of ortho ring while it destroys aromaticity of meta ring. Aromaticity variations are determined by symmetry governed rotational excitations of frontier π orbitals. The parallel orientation reveals a substantial reduction of local aromaticity verified with NICSπ analysis and electron delocalization indices.

Charistos* N. D., Muñoz-Castro* A.

Induced Magnetic Field in sp-Hybridized Carbon Rings: Analysis of Double Aromaticity and Antiaromaticity in Cyclo[2n]carbon Allotropes

Physical Chemistry Chemical Physics 2020, 22 , 9240-9249 , DOI: 10.1039/D0CP01252A 2020 PCCP HOT Article

The induced magnetic field of C_2N (N = 3-14) carbon rings was dissected to contributions from out-of-plane and in-plane π orbitals revealing two concurrent long-range shielding or deshielding cones as a manifestation of the dual aromatic and antiaromatic character of C_4n+2 and of C_4n rings respectively. Aromaticity based on the magnetic criterion was evaluated with regard to bonding pattern and geometrical characteristics elucidating the influence of bond length and bond angle alternation on out-of-plane and in-plane magnetic response. Ground state polyynic geometries of C_4n+2 rings exhibit comparable shielding cones to annulenes, decreasing magnetic response with regard to ring size and similar π_out and π_in diatropicity. Transition state cumulenic rings display increased aromaticity expressed by a constant very strong magnetic response and augmented π_out diatropicity with regard to π_in. The variations of the induced magnetic field are explained on the basis of frontier orbital interactions through rotational excitations, which enable further rationalization of the aromatic/antiaromatic behavior.

Charistos* N. D., Muñoz-Castro* A.

Double aromaticity of B₄₀ Fullerene: Induced magnetic field analysis of π and σ delocalization in boron cavernous structure

Physical Chemistry Chemical Physics 2019, 21 , 20232-20238 DOI: 10.1039/C9CP04223G

The induced magnetic field of B₄₀ was dissected to contributions from π, σ and core electrons revealing the origins for the formation of the strong long range shielding response characterizing the spherical aromatic nature of the cavernous D_2d structure. Our analysis showed a complementary role of π and σ orbitals for the formation of the global shielding cone, with weak π contributions at long range and strong σ contributions inside the cage, supporting the molecule as double aromatic with weak π and strong σ delocalization. Similar local variations of both π and σ magnetic response were identified portraying peripheral diatropic and local paratropic currents. The weak π aromaticity is explained on the basis of symmetry rules pertaining its electronic structure which forbid small gap paratropic rotational excitations.

Charistos* N. D., Muñoz-Castro* A. and Sigalas M. P.

The pseudo-π model of the Induced Magnetic Field: Fast and Accurate Visualization of Shielding and Deshielding Cones in Planar Conjugated Hydrocarbons and Spherical Fullerenes

Physical Chemistry Chemical Physics 2019, 21, 6150-6159 DOI: 10.1039/C9CP00836E

Supplementary Material: Interactive Explorable Visualizations

The induced magnetic fields originating from the π system of planar conjugated polycyclic hydrocarbons and spherical fullerenes are accurately reproduced by their corresponding hydrogen skeletal models (HSMs). Moreover, the individual contribution per molecular orbital is also reproduced unraveling simple symmetry rules related to canonical molecular orbitals. Hence, fast, handy and accurate 3D visualization of shielding and deshielding cones is realized, enabling the interpretation of global and local π aromaticity and antiaromaticity of PAHs and spherical species in a simple and concise manner to facilitate further interpretations of large sized hydrocarbon systems.

Charistos* N. D. and Muñoz-Castro* A.

Τhe Induced Magnetic Field of Fullerenes. Role of σ- and π- contributions to Spherical Aromatic, Non-Aromatic and Antiaromatic Character in C₆₀^q (q = +10, 0, -6, -12), and Related Alkali-Metal Decorated Building Blocks, Li₁₂C₆₀ and Na₆C₆₀

Journal of Physical Chemistry C 2018, 122 (17) , 9688-9698 DOI: 10.1021/acs.jpcc.8b02419

The induced magnetic field of fullerenes is strongly dependent on the charge state, where C₆₀ is depicted as a nonaromatic species, in contrast to C₆₀¹⁰⁺ which exhibits a strong spherical aromatic character. Here, we account for the response of relevant charged stable building blocks for novel extended networks with variable applications, as observed in A₁₂C₆₀ and A₆C₆₀ phases (A = alkali metal), given by, Li₁₂C₆₀ and Na₆C₆₀, as well as four different charge states of C₆₀^q (q = +10, 0, −6, −12), to an external magnetic field is studied in detail, focusing on the contributions from the π and σ systems to the induced magnetic field. C₆₀, C₆₀^6–, and C₆₀^12– accounts for the variation of their isolated species upon addition of charge, whereas C₆₀¹⁰⁺ is a hypothetical highly aromatic counterpart. Our results show that each spherical shell and each canonical molecular orbital exhibit characteristic patterns, revealing the direct dependence of the magnetic response, and therefore of spherical aromatic character, with regard to electron configuration. In particular, low-lying S, P, D, and F π-type shells exhibit identical strong and long-range shielding character among the four charge states. The G shell exhibits a weak shielding response, precluding the strong deshielding contribution from high-lying H and I shells. A similar analysis is given for σ-type orbitals. Thus, the aromatic, nonaromatic, and antiaromatic character of C₆₀ among the different charge states is ruled by the population of the high-lying π-shells, which is explained in terms of π → π* excitations of high-lying canonical molecular orbitals.

Charistos* N. D., Papadopoulos A., Nikopoulos T, Muñoz-Castro A. and Sigalas* M.

Canonical Orbital Contributions to the Magnetic Fields Induced by Global and Local Diatropic and Paratropic Ring Currents

Journal of Computational Chemistry 2017, 38 (30) , 2594-2604 DOI: 10.1002/jcc.24917

The induced magnetic field (IMF) of naphthalene, biphenyl, biphenylene, benzocyclobutadiene, and pentalene is dissected to contributions from the total π system, canonical π‐molecular orbitals (CMO), and HOMO→π* excitations, to evaluate and interpret relative global and local diatropicity and paratropicity. Maps of the IMF of the total π system reveal its relative strength and topology that corresponds to global and local diatropic and paratropic ring currents. The total π magnetic response is determined by this of canonical HOMOs and particularly by paratropic contributions of rotational excitations from HOMOs to unoccupied π* orbitals. Low energy excitations and similar nodal structure of HOMO and π* induce strong paratropic fields that dominate on antiaromatic rings. High energy excitations and different nodal structures lead to weak paratropic contributions of canonical HOMOs, which are overwhelmed by diatropic response of lower energy canonical orbitals in aromatic rings. CMO‐IMF analysis is found in agreement with ring current analysis.

Papadopoulos A. G., Charistos* N. D. and Muñoz-Castro* A.

Magnetic Response of Aromatic Rings Under Rotation: Aromatic Shielding Cone of Benzene Upon Different Orientations of the Magnetic Field

ChemPhysChem 2017, 18 (12) , 1499–1502 DOI: 10.1002/cphc.201700279

The induced shielding cone is one of the most characteristic aspects of aromatic species. Herein, we explore its behavior under different orientations of the applied magnetic field by evaluating the overall and dissected π‐ and σ‐electron contributions. Our results shed light onto the orientation dependence behavior of the shielding cone, unraveling a characteristic pattern upon rotation of the aromatic ring. This pattern decreases the long range of the magnetic response, such that it resembles the behavior under constant molecular tumbling in solution.

Charistos* N. D., Papadopoulos A. G. and Sigalas* M.

Interpretation of electron delocalization in benzene, cyclobutadiene, and borazine based on visualization of individual molecular orbital contributions to the induced magnetic field

Journal of Physical Chemistry A 2014 , 118 (6) , 1113–22 DOI: 10.1021/jp411410r

The magnetic response of the valence molecular orbitals (MOs) of benzene, cyclobutadiene, and borazine to an external magnetic field has been visualized by calculating the chemical shielding in two-dimensional grids of points on the molecular plane and on a plane perpendicular to it, using gauge-including atomic orbitals (GIAOs). The visualizations of canonical MO contributions to the induced magnetic field (CMO-IMF) provide a clear view of the spatial extension, the shape, and the magnitude of shielding and deshielding areas within the vicinity of the molecule, originating from the induced currents of each valence orbital. The results are used to investigate the delocalization of each valence MO and to evaluate its contribution to the aromatic character of systems under study. The differentiation of the total magnetic response among the three molecules originates exclusively from π-HOMO orbitals because the magnetic response of the subsets of the remaining MOs is found to be almost identical. Borazine is classified as nonaromatic as the four electrons that occupy the π-HOMO are found to be strongly localized on nitrogen centers. CMO-IMF can clarify the interpretation of various NICS indexes and can be applied for the investigation of various types of electron delocalization.

Papers

2024

R. Lingas, N. D. Charistos* and A. Muñoz-Castro*
BOROSPHERENE IN THE NANOHOOP: Complexation and Aromaticity of Neutral and Dioxidized Cycloparaphenylene Supramolecules with B₄₀ And C₆₀ Fullerenes
Chemistry - A European Journal 2023, e202402027, DOI: 10.1002/chem.202402027

2023

R. Lingas, N. D. Charistos* and A. Muñoz-Castro*
Charge Delocalization and Aromaticity of Doubly Reduced Double-walled Carbon Nanohoops
Physical Chemistry Chemical Physics 2023, 25, 19481-19491, DOI: 10.1039/D3CP01994B 2023 PCCP HOT Article
R. Lingas, N. D. Charistos* and A. Muñoz-Castro*
Local and Global Aromaticity under Rotation. Analysis of Two- and Three-Dimensional Representative Carbon Nanostructures
Physical Chemistry Chemical Physics 2023, 25, 14285-14293, DOI: 10.1039/D3CP00569K

2022

Mesías Orozco-Ic,* Nickolas D. Charistos, Alvaro Muñoz-Castro, Rafael Islas, Dage Sundholm,* and Gabriel Merino*
Core-electron contributions to the molecular magnetic response
Physical Chemistry Chemical Physics 2022, 24, 12158-12166, DOI: 10.1039/D1CP05713H

2021

R. Lingas, N. D. Charistos* and A. Muñoz-Castro*
Aromaticity of ortho and meta 8-cycloparaphenylene and their dications: Induced magnetic field analysis with localized and delocalized orbitals in strained nanohoops
ChemPhysChem 2021, 22(8), 741-751, DOI: 10.1002/cphc.202100057

2020

P. L. Rodríguez-Kessler, N. D. Charistos, R. B. King* and A. Muñoz-Castro*
On the Formation of Spherical Aromatic Endohedral Buckminsterfullerene. Evaluation of M@C₆₀ (M=Cr, Mo, W) From Relativistic DFT Calculations
Physical Chemistry Chemical Physics 2020, 22, 14268-14275, DOI: 10.1039/D0CP02475A
N. D. Charistos* and A. Muñoz-Castro*
Induced Magnetic Field in sp-Hybridized Carbon Rings: Analysis of Double Aromaticity and Antiaromaticity in Cyclo[2n]carbon Allotropes
Physical Chemistry Chemical Physics 2020, 22, 9240-9249, DOI: 10.1039/D0CP01252A 2020 PCCP HOT Article
M. Orozco-Ic, J. Barroso, N. D. Charistos, A. Muñoz-Castro* and G. Merino*
Consequences of the curvature on the induced magnetic field: Case of helicenes
Chemistry—A European Journal 2020, 26 (1), 326-330, DOI: 10.1002/chem.201904390 Very Important Paper

2019

Charistos* N. D., Muñoz-Castro* A.
Double aromaticity of B₄₀ Fullerene: Induced magnetic field analysis of π and σ delocalization in boron cavernous structure
Physical Chemistry Chemical Physics 2019, 21 (36), 20232-20238, DOI: 10.1039/C9CP04223G
Karamanis* P., Charistos N. D., Sigalas M. P. and Rérat M.
Polyaromatic Systems Combining Increasing Optical Gaps and Amplified Nonlinear Optical Properties. A Comprehensive Theoretical Study on B₃N₃ Doped Nanographenes
The Journal of Physical Chemistry C 2019, 123 (34), 21135-21149, DOI: 10.1021/acs.jpcc.9b05543
Charistos* N. D., Muñoz-Castro* A. and Sigalas M. P.
The pseudo-π model of the Induced Magnetic Field: Fast and Accurate Visualization of Shielding and Deshielding Cones in Planar Conjugated Hydrocarbons and Spherical Fullerenes
Physical Chemistry Chemical Physics 2019, 21, 6150-6159 DOI: 1039/C9CP00836E
Charistos N. D., Jin P. and Muñoz-Castro* A.
Aromatic Character of O_h-C₂₄N₂₄. A Cavernous Nitride Fullerene Bearing N₄-Macrocycle Motifs
International Journal of Quantum Chemistry 2019 DOI: 1002/qua.25919
Ortolan O. A., Charistos N. D, Guajardo-Maturana R., Olea C., Caramori G. F., Parreira R. and Muñoz-Castro A.
On the Cation-π Capabilities of Small all sp²-Carbon Host Structures. Evaluation of [6.8]₃Cyclacene from Relativistic DFT Calculations
International Journal of Quantum Chemistry 2019, 119(4), e25811 DOI: 1002/qua.25811

2018

Charistos* N. D. and Muñoz-Castro* A.
The Induced Magnetic Field of Fullerenes. Role of σ- and π- contributions to Spherical Aromatic, Non-Aromatic and Antiaromatic Character in C₆₀^q (q = +10, 0, -6, -12), and Related Alkali-Metal Decorated Building Blocks, Li₁₂C₆₀ and Na₆C₆₀.
Journal of Physical Chemistry C 2018, 122 (17), 9688-9698 DOI: 1021/acs.jpcc.8b02419

2017

Charistos* N. D., Papadopoulos A., Nikopoulos T, Muñoz-Castro A. and Sigalas* M.
Canonical Orbital Contributions to the Magnetic Fields Induced by Global and Local Diatropic and Paratropic Ring Currents.
Journal of Computational Chemistry 2017, 38 (30), 2594–2604 DOI: 1002/jcc.24917
Papadopoulos A. G, Charistos* N. D. and Muñoz-Castro* A.
Magnetic Response of Aromatic Rings Under Rotation: Aromatic Shielding Cone of Benzene Upon Different Orientations of the Magnetic Field.
ChemPhysChem 2017, 18 (12), 1499–1502 DOI: 1002/cphc.201700279

2016

Papadopoulos A. G., Charistos* N. D.. and Muñoz-Castro* A.
On the Role of Heteroatoms in Aromatic Rings. Insights from 10π Main Group Elements Heterorings [(EH)₂S₂N₄]^q (E = C, P, B, Si, Al and q = 0, −2).
New Journal of Chemistry 2016, 40 (6), 5090–5098 DOI: 10.1039/C5NJ03573B

2015

A. G. Papadopoulos, N. D. Charistos, K. Kyriakidou and M.P. Sigalas*
Study of Electron Delocalization in 1,2-, 1,3-, and 1,4-Azaborines Based on the Canonical Molecular Orbital Contributions to the Induced Magnetic Field and Polyelectron Population Analysis.
Journal of Physical Chemistry A 2015, 119(39), 10091–10100 DOI: 1021/acs.jpca.5b06027

2014

N. D. Charistos*, A. G. Papadopoulos and M. P. Sigalas*
Interpretation of electron delocalization in benzene, cyclobutadiene, and borazine based on visualization of individual molecular orbital contributions to the induced magnetic field.
Journal of Physical Chemistry A 2014, 118(6), 1113–22 DOI: 1021/jp411410r
Antonoglou L. D., Kostelidou T. N., Charistos N. D., Sigalas* M. P.
Investigating Chemistry Students’ Skills to Mentally Manipulate (Rotation & Reflection) 2D Symbolic Molecular Representations.
Procedia - Social and Behavioral Sciences 2014, 152, 517–522 DOI: 1016/j.sbspro.2014.09.208
Koutalas V. G., Antonoglou L. D., Charistos N. D., Sigalas* M. P.
Investigation of Students’ Ability to Transform and Translate 2D Molecular Diagrammatic Representations and Its Relationship to Spatial Ability and Prior Chemistry Knowledge.
Procedia - Social and Behavioral Sciences 2014, 152, 698–703 DOI: 1016/j.sbspro.2014.09.265

2012

Papadopoulos A. G., Charistos N. D., Sigalas* M. P.
Aromaticity Variation in BN Substituted Triphenylene: A Theoretical Study.
AIP Conference Proceedings 2012, 1504, 1223–1226 DOI: 1063/1.4772148

2011

L.D. Antonoglou, N.D. Charistos and M.P. Sigalas*
Design, development and implementation of a technology enhanced hybrid course on molecular symmetry: Students' outcomes and attitudes.
Chemistry Education Research and Practice 2011, 12(4), 454-468 DOI: 1039/C0RP90013C

2008

D. Antonoglou, N.D. Charistos, M.P. Sigalas*
Design of Molecular Visualization Educational Software for Chemistry Learning.
In T.B. Scott and J. I. Livingston (Eds) Leading-Edge Educational Technology, 55 – 81, Nova Puplishers, New York, 2008
A. Tsipis*, C. E. Kefalidis and N. D. Charistos.
Ligand-Effects on the Stability, Conformational Preference and Diatrophic Response of 3- Membered Hydrocopper Rings.
In T. W. Cartere and K. S. Verley (Eds), Coordination Chemistry Research Progress, 201 – 215, Nova Puplishers, New York, 2008
A. Tsipis* and N. D. Charistos
How the Aromatic 4-Membered Hydrido-Bridged Copper Rings Respond to Successive Nucleophilic Attack?
The Open Mechanical Engineering Journal 2008, 2, 12 DOI: 10.2174/1874155X00802010012

2005

N. D. Charistos, C.A. Tsipis and M. P. Sigalas*
3D Molecular Symmetry Shockwave: A Web Application for Interactive Visualization and Three-Dimensional Perception of Molecular Symmetry.
Journal of Chemical Education 2005, 82, 1741 DOI: 10.1021/ed082p1741.2

2004

N. D. Charistos, C.A. Tsipis and M. P. Sigalas*
3DNormalModes Shockwave. Three Dimensional Perception of Molecular Normal Modes on the Web.
Journal of Chemical Education 2004, 81, 1231 DOI: 10.1021/ed081p1231.2

2003

N. D. Charistos, V.I. Teberekidis, C.A. Tsipis and M.P. Sigalas*
Design and Development of a Multimedia Educational Tool for Interactive Visualization and Three Dimensional Perception of Vibrational Spectra Data of Molecules.
Education and Information Technologies 2003, 8, 369 DOI: 10.1023/B:EAIT.0000008677.08249.98
P. Sigalas*, N. D. Charistos, V.I. Teberekidis and C. A. Tsipis
3DNormalModes 1.0.
Journal of Chemical Education 2003, 80, 1222 DOI: 10.1021/ed080p1222.2

International Conferences

2017

A. G. Papadopoulos, N. D. Charistos, M. P. Sigalas.
Visualization of molecular orbitals contributions to the induced magnetic field of heterocyclic isocoronene analogues.
25th Conference on Current Trends in Computational Chemistry, November 2017, Jackson, MS, United States

2015

A. G. Papadopoulos, N. D. Charistos, A. Arvanitidis, M. P. Sigalas.
Visualization of the canonical molecular orbital contributions to the induced magnetic field of B‐Trisubstituted Borazines.
15th International Congress of Quantum Chemistry, June 2015, Beijing, China
N. D. Charistos, A. G. Papadopoulos, T. A. Nikopoulos, M. P. Sigalas.
Visualization of Differences and Similarities of the Magnetic Response of π and σ- Molecular Orbitals in Seven-Membered Boron Wheels.
10th Congress of the World Association of Theoretical and Computational Chemists, WATOC, October 2014, Santiago, Chile

2014

A. G. Papadopoulos, N. D. Charistos, A. G. Arvanitidis, M. P. Sigalas.
Substituents' Effects on π Electron Delocalization in B-Trisubstituted Borazines Based on Visualization of Molecular Orbitals' Contributions to the Induced Magnetic Field.
10th Congress of the World Association of Theoretical and Computational Chemists, WATOC, October 2014, Santiago, Chile
N. D. Charistos, Maria Palassopoulou, and Michael P. Sigalas.
Teaching Structural Biochemistry Using Jmol Based Interactive Molecular Visualization Material and Protein Data Bank.
12th European Conference on Research in Chemistry Education, ECRICE, July 2014, Jyväskylä, Finland
G. Koutalas, L. D. Antonoglou, N. D. Charistos, M. P. Sigalas.
How students translate and transform molecular diagrammatic representations? A study based on matching items questionnaires, eye movements’ patterns and verbal explanations.
12th European Conference on Research in Chemistry Education, ECRICE, July 2014, Jyväskylä, Finland

2013

P. Sigalas, N. D. Charistos, V. Koutalas, M. Palassopoulou and L.D. Antonoglou.
Molecular Visualization in Chemistry Education. From symmetry principles to platonic solids, transition metal complexes and proteins’ structure.
First African Conference on Research In Chemistry Education [ACRICE-1], 2013 Adis Ababa, Ethiopia

2012

D. Antonoglou, N. D. Charistos, M. P. Sigalas.
Exploring Criteria for Selecting Proper Orientations of 2D and 3D Molecular Representations in Chemistry Education.
11th European Conference on Research in Chemistry Education, ECRICE, July 2012, Rome, Italy

2011

A. G. Papadopoulos, N. D. Charistos, M. Sigalas.
Molecular Orbital Contributions to the Induced Magnetic Field οf Benzene, Cyclobutadiene, Borazine, 1,2-, 1,3- and 1,4-Azaborines.
9th Triennial Congress of the World Association of Theoretical and Computational Chemists, WATOC, July 2011, Sandiago de Compostela, Spain

2010

N. D. Charistos, L. D. Antonoglou, V. Koutalas and M. P. Sigalas.
Design of Molecular Visualization Educational Software for Learning and Teaching Molecular Symmetry: From Learning Objects to Online Course Material.
10th European Conference on Research in Chemistry Education, ECRICE, July 2010, Krakow, Poland
D. Antonoglou, N.D. Charistos, M.P. Sigalas.
Design, Development, Implementaton and Assessment of a Hybrid Course on Molecular Symmetry — A pilot project.
The 4th International Conference Research in Didactics of the Sciences, DidSci, July 2010, Krakow, Poland

2009

L. Antonoglou, V. Koutalas, M. Palassopoulou, N. D. Charistos, M. Sigalas.
Molecular Visualization in Chemistry Education. From symmetry principles to platonic solids, transition metal complexes and proteins' structure.
Gordon Research Conference on Visualization in Science and Education, GRC, July 2009, Magdalen College, Oxford, UK

2008

P. Sigalas and N. D. Charistos.
3DMolSym - Chemistry Classic Award Winner.
MERLOT International Conference, August 2008, Minneapolis USA

2005

N. D. Charistos and M. P. Sigalas.
Standalone and Web Applications for Interactive Visualization and Three Dimensional Perception of Molecular Symmetry Elements and Normal Modes.
Gordon Research Conference on Visualization in Science and Education, GRC, July 2005, Queen's College, Oxford, UK
N. D. Charistos and M. P. Sigalas.
Standalone and Web Applications for Interactive Visualization and Three Dimensional Perception of Molecular Symmetry Elements and Normal Modes.
International Conference on Computational Methods in Sciences and Engineering, ICCMSE, October 2005, Lutraki, Greece

2002

N. D. Charistos, V.I. Teberekidis, C.A. Tsipis, M.P. Sigalas.
3DNormalModes: A program for Three Dimensional Perception of Normal Modes.
6th World Congress of Theoretically Oriented Chemists, WATOC, 2002, Lugano, Switzerland
N. D. Charistos, V.I. Teberekidis, C.A. Tsipis, M.P. Sigalas.
Development of Educational Programs for Visualization and Three Dimensional Perception of Symmetry Elements and Normal Modes of Vibration.
4th European Conference on Computational Chemistry, EUCO-CC4, 2002, Assisi, Italy

National (Greek) Conferences

2019

Δ. Γανίτη, Λ. Πασσιάς, Μ.-Π. Βλαχολιά, Β. Κουταλάς, Ν. Χαριστός, Μ. Σιγάλας
Αξιολόγηση Ευχρηστίας και Αποτελεσματικότητας Γνωστικού Εργαλείου Σχεδίασης και Χειρισμού Συντακτικών Τύπων Οργανικών Ενώσεων
11^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, Φλώρινα, 2019

2017

Β. Κουταλάς, Π. Κατικαρίδου, Ν. Χαριστός, Μ. Σιγάλας
Εφαρμογή Τεχνικών Οφθαλμικών Καταγραφών για τη Μελέτη Χειρισμού και Επεξεργασίας της Πληροφορίας από Χρήστες Πολυαναπαραστασιακού Εκπαιδευτικού Περιβάλλοντος με Αντικείμενο τις Προβολές Fischer & Newman
10^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, Ρέθυμνο, 2017
Ν. Χαριστός, Β. Κουταλάς, Μ. Βλαχολιά, Κ. Σάλτα, Χ. Τζουγκράκη, Μ. Σιγάλας
2DrawChemQuiz: Σχεδιασμός, ανάπτυξη και εφαρμογή ενός γνωστικού εργαλείου εξάσκησης στη σχεδίαση και χειρισμό συντακτικών τύπων
10^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, Ρέθυμνο, 2017

2015

Α. Βουκλής, Ε. Παρισοπούλου, Ν. Χαριστός, Α. Γιαννακουδάκης, Π. Γιαννακουδάκης
Η Χρησιμοποίηση των Δυνατοτήτων του CMS Joomla στο Σχεδιασμό και Υλοποίηση Ιστότοπου με Θέμα την Ηλεκτροχημεία.
8^o Πανελλήνιο Συνέδριο των Εκπαιδευτικών για τις ΤΠΕ, 26‐28 Ιουνίου, Σύρος, 2015.
Β. Γ. Κουταλάς, Ν. Δ. Χαριστός, Μ. Π. Σιγάλας.
Σχεδιασμός και Ανάπτυξη Εκπαιδευτικού Ιστότοπου με Δυναμικά Διασυνδεόμενες Μοριακές Αναπαραστάσεις για την Κατανόηση των Προβολών Fischer και Newman.
8o Πανελλήνιο Συνέδριο των Εκπαιδευτικών για τις ΤΠΕ, 26‐28 Ιουνίου, Σύρος, 2015.
Β. Γ. Κουταλάς, Λ. Δ. Αντώνογλου, Ν. Δ. Χαριστός, Μ. Π. Σιγάλας.
Βαθμός Κατανόησης και Ευχέρεια Χειρισμού Δισδιάστατων Διαγραμματικών Μοριακών Αναπαραστάσεων και Ανάπτυξη Εκπαιδευτικού Λογισμικού για τη Βελτίωση τους.
12^o Συνέδριο Χημείας Ελλάδος Κύπρου, Θεσσαλονίκη, 2015
Α. Γ. Παπαδόπουλος, Ν. Δ. Χαριστός, Α. Αρβανιτίδης, Μ. Π. Σιγάλας.
Οπτικοποίηση και ανάλυση της επίδρασης της υποκατάστασης στον π- ηλεκτρονιακό απεντοπισμό σε Β-τριυποκατεστημένες βοραζίνες.
12^o Συνέδριο Χημείας Ελλάδος Κύπρου, Θεσσαλονίκη, 2015
Ν. Δ. Χαριστός, Α. Γ. Παπαδόπουλος, Θ. Νικόπουλος, Μ. Π. Σιγάλας.
Οπτικοποίηση και ανάλυση της μαγνητικής απόκρισης των π- και σ- μοριακών τροχιακών επταμελών μοριακών τροχών βορίου.
12^o Συνέδριο Χημείας Ελλάδος Κύπρου, Θεσσαλονίκη, 2015
Β. Γ. Κουταλάς, Λ. ∆. Αντώνογλου, Ν. ∆. Χαριστός, Μ. Π. Σιγάλας.
∆ιερεύνηση των δυσκολιών που αντιµετωπίζουν οι φοιτητές στην κατανόηση και το νοητικό χειρισµό δισδιάστατων διαγραµµατικών µοριακών αναπαραστάσεων
9^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστηµών και Νέων Τεχνολογιών στην Εκπαίδευση, Θεσσαλονίκη, 2015
Α. Βουκλής, Ε. Παρισοπούλου, Ν. Χαριστός, Α. Γιαννακουδάκης, Π. Γιαννακουδάκης.
∆ιερεύνηση των Απόψεων των Φοιτητών Σχετικά µε τη Μελέτη και την Κατανόηση Της Ηλεκτροχηµείας µέσω Χρήσης Εκπαιδευτικού Ιστοτόπου και Κατάλληλα Σχεδιασµένων Ερωτήσεων Αυτοαξιολόγησης.
9^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστηµών και Νέων Τεχνολογιών στην Εκπαίδευση, Θεσσαλονίκη, 2015
Β. Γ. Κουταλάς, Ν. ∆. Χαριστός, Μ. Π. Σιγάλας.
Σχεδιασµός και Ανάπτυξη Εκπαιδευτικού Λογισµικού Χειρισµού Τρισδιάστατων Μοριακών Μοντέλων και ∆ισδιάστατων ∆ιαγραµµατικών Αναπαραστάσεων µε Αντικείµενο τις Προβολές Fischer και Newman.
9^ο Πανελλήνιο Συνέδριο στη Διδακτική των Φυσικών Επιστηµών και Νέων Τεχνολογιών στην Εκπαίδευση, Θεσσαλονίκη, 2015

2013

Λ. Αντώνογλου, , Θ. Κωστελίδου, Ν. Χαριστός, Μ. Σιγάλας.
Διερεύνηση Οπτικοχωρικής Ικανότητας Φοιτητών Χημείας. Εργαλεία Εκτίμησης Δεξιοτήτων Νοητικής Οπτικοποίησης και Χειρισμού της Τρισδιάστατης Μοριακής Δομής.
8^ο Πανελλήνιο Συνέδριο Διδακτικής των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, Βόλος, 2013
B. Κουταλάς, N. Γιωργάς, N. Χαριστός, M. Σιγάλας.
Επανασχεδιασμός του εκπαιδευτικού λογισμικού για το μάθημα της Χημείας Γ΄ Γυμνάσιου «Ο Θαυμαστός Κόσμος της Χημείας» με την αξιοποίηση των δυνατοτήτων ενός σύγχρονου συστήματος διαχείρισης περιεχομένου.
10^o Συνέδριο Ε.Ε.Ε.Π. - Δ.Τ.Π.Ε - Η Εκπαίδευση στην Εποχή των ΤΠΕ, Αθήνα, 2013

2011

Λ.Δ. Αντώνογλου, Ν.Δ. Χαριστός, Μ.Π. Σιγάλας.
Διερεύνηση της δεξιότητας της νοητικής μεταφοράς ανάμεσα σε Tρισδιάστατες & Δισδιάστατες αναπαραστάσεις της τετραεδρικής μοριακής δομής από φοιτητές Χημείας.
7ο Πανελλήνιο Συνέδριο Διδακτικής των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση (ΚΟΔΙΦΕΕΤ), Αλεξανδρούπολη, 2011
Ν. Δ. Χαριστός, Α.Γ. Παπαδόπουλος, Θ. Νικόπουλος, M.Π. Σιγάλας.
Οπτικοποίηση της Συνεισφοράς των Μοριακών Τροχιακών στο Επαγόμενο Μαγνητικό Πεδίο Επίπεδων Κυκλικών Μορίων.
21ο Πανελλήνιο Συνέδριο Χημείας, Θεματική Ενότητα: Φυσική και Θεωρητική Χημεία, Θεσσαλονίκη, 2011
Λ. Αντώνογλου, Ν. Χαριστός, Μ. Σιγάλας.
Διερεύνηση της ικανότητας φοιτητών χημείας στο νοητικό χειρισμό και τη μετάφραση 2D και 3D μοριακών οπτικοποιήσεων.
21ο Πανελλήνιο Συνέδριο Χημείας, Θεματική Ενότητα: Χημεία και Εκπαίδευση, Θεσσαλονίκη, 2011

2010

Λ.Δ. Αντώνογλου, Ν.Δ. Χαριστός, Μ.Π. Σιγάλας.
Σχεδιασμός, ανάπτυξη, εφαρμογή και αξιολόγηση της αποτελεσματικότητας του υβριδικού μοντέλου διδασκαλίας της μοριακής συμμετρίας.
7ο Πανελλήνιο Συνέδριο με Διεθνή Συμμετοχή, Οι ΤΠΕ στην Εκπαίδευση - Ελληνική Επιστημονική Ένωση Τεχνολογιών Πληροφορίας & Επικοινωνιών στην Εκπαίδευση (ΕΤΠΕ), Κόρινθος, 2010

2009

Λ.Δ. Αντώνογλου, Ν.Δ. Χαριστός, Μ.Π. Σιγάλας.
Σχεδιασμός & Ανάπτυξη Υβριδικού Μοντέλου Διδασκαλίας της Μοριακής Συμμετρίας με Χρήση Τρισδιάστατης Μοριακής Οπτικοποίησης.
6ο Πανελλήνιο Συνέδριο Διδακτικής των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, (ΚΟΔΙΦΕΕΤ), Φλώρινα, 2009
Μ. Παλασοπούλου, Ν. Χαριστός, Μ. Σιγάλας
Τρισδιάστατη Οπτικοποίηση των Πρωτεϊνών ως Εκπαιδευτικό Εργαλείο σε Περιβάλλον WWW.
6ο Πανελλήνιο Συνέδριο Διδακτικής των Φυσικών Επιστημών και Νέων Τεχνολογιών στην Εκπαίδευση, (ΚΟΔΙΦΕΕΤ), Φλώρινα, 2009

2006

Μ. Σιγάλας, Α. Γιαννακουδάκης, Χ. Τσουγκράκη, Β. Αγγελόπουλος, Α. Τζαμτζής, Ν. Χαριστός και Λ. Δ. Αντώνογλου. Υποστηρικτικό Εκπαιδευτικό Λογισμικό για το Μάθημα της Χημείας Γυμνασίου.
5^ο Πανελλήνιο Συνέδριο Ε.Τ.Π.Ε., “Oι Τεχνολογίες της Πληροφορίας και των Επικοινωνιών στην Εκπαίδευση”, Θεσσαλονίκη, 2006
Ν. Δ. Χαριστός και Μ. Π. Σιγάλας.
Ανάπτυξη Εκπαιδευτικού Λογισμικού Μοριακής Μοντελοποίησης και Εφαρμογή του σε Θέματα Συμμετρίας και Κανονικών Τρόπων Δόνησης των Μορίων.
5^ο Πανελλήνιο Συνέδριο Ε.Τ.Π.Ε., “Oι Τεχνολογίες της Πληροφορίας και των Επικοινωνιών στην Εκπαίδευση”, Θεσσαλονίκη, 2006

2004

Ν. Δ. Χαριστός, Κ.Α. Τσίπης, Μ. Π. Σιγάλας.
Χρήση Τεχνολογιών Τρισδιάστατων Γραφικών για τη Μοντελοποίηση και Τρισδιάστατη Απεικόνιση των Κανονικών Τρόπων Δόνησης και της Συµµετρίας των Μορίων. 2ο Πανελλήνιο Συνέδριο “Πληροφορική και Εκπαίδευση”, Θεσσαλονίκη, 2004

Software Development

MIMAF

Computational Chemistry Tool

ADF output processing and molecular visualization of contour maps and vector maps of Molecular Induced Magnetic Fields

2008-2019

2DrawChem

Educational Chemistry Software and Research Tool

Chemical structural formulas modelling and drawing software. Development of interactive structural formulas chemistry problems

2013-2015

MIE (Matching Items Environment)

Educational Chemistry Research Tool

Interactive Digital Instruments for the assesment of visuospatial thinking in chemsitry problem solving

2013

Molix3D

Educational Chemistry Software

Software package for the molecular visualization of polymers, isomers, enantiomers, peptides and functional groups

2007

iFreq3D

Computational Chemistry Tool

Gaussian output processing and molecular visualization of NICS-scan diagrams

2006

juniorLab

Educational Chemistry Software

Chemistry Laboratory Simulation

2005

3DMolSym

Educational Chemistry Software

Molecular visualization of symmetry elements and symmetry operations

2004

Download

3DNormalModes

Educational Chemistry Software

Molecular visualization of normal modes of vibrations

2003

Download

Web Design and Development

ACC2023

acc2023.chem.auth.gr/

2023

CHEMNOESIS

chem.noesis.edu.gr

2022

Nick's JSmol Tutorials

users.auth.gr/nicharis/jmoltutorial

2019 -

Exploring Proteins

molwave.chem.auth.gr/proteins

2014

The Fabulous World of Chemistry

molwave.chem.auth.gr/fabchem

2013

Topics in History of Chemistry

molwave.chem.auth.gr/chemhistory

2012

International Year of Chemistry 2011

molwave.chem.auth.gr/iyc2011

2011

Computational Chemistry Video Tutorials (in Greek)

Lab 1 - Z-Matrix & GaussView

Lab 2 - Μοριακή Μηχανική

Lab 3 - Σύνολα Βάσης

Lab 4 - Βελτιστοποίηση Γεωμετρίας - Σάρωση PES

Lab 5 - Μοριακές Ιδιότητες - Οπτικοποίηση

Lab 6 - Κανονικοί Τρόποι Δόνησης

Teaching 2021-22

External Collaborators

Prof. Alvaro Muñoz-Castro / Universidad Autónoma de Chile

Testzone - Fun Stuff

Chemical Reaction Simulator (working example)

Canvas/Javascript/HTML5

Chemical reaction simulation based on particle elastic collision.

2019 (work in progress)

Pseudo-Pi Model

JSmol webpage

Interactive Explorable Visualizations of Induced Magnetic Field Isosurfaces with JSmol

2018

Wave Superposition Simulation

Canvas/Javascript/HTML5

Manipulating simple sliders the user can adjust the wavelength, the frequency and the amplitude of two animated sine waves, visualize the resulting sum and explore related scientific concepts.

2011

Diatomic Motion Simulation

Canvas/Javascript/HTML5

A simple interactive animation of translational, rotational and vibrational motion of a diatomic molecule.

2011

Research Grants

Design and development of online educational chemistry software

Student's scientific literacy development in formal and informal education with the use of virtual laboratories.

Principal Investigator

2018-2021

ID 97155

Awards

2012

Award of Excellence

Ministry of Education

Athens

2010

2nd Panhellenic Award of Poetry «Kouros Evropou»

Ministry of Culture, "Art" Macedonian Artistic Corporation

Kilkis

2009

Award of Innovation

Aristotle University of Thessaloniki

Thessaloniki

2008

MERLOT Chemistry Classics

Multimedia Educational Resource for Learning and Online Teaching

Minneapolis, USA

2004

Exemplarchem Overall Winner 1999-2004

Royal Society of Chemistry (RSC)

London, UK

2004

Exemplarchem

Chemical Abstracts Service (CAS)

London, UK