4N electron aromatic cycles in polycyclic hydrocarbons

Literature Information

Publication Date 2017-05-18
DOI 10.1039/C7CP02288C
Impact Factor 3.676
Authors

Michael Mauksch, Svetlana B. Tsogoeva


View Original

Abstract

Polycyclic fully conjugated hydrocarbons in which aromatics are fused to aromatics – or aromatics to antiaromatics – are important as potential organic semiconductors. Herein we explore the only remaining fusion pattern of antiaromatics to antiaromatics. It is shown computationally that the central antiaromatic unit (cyclobutadiene or pentalene) in such a three-unit polycyclic hydrocarbon, generated by fusion of three antiaromatic molecules, turns aromatic according to magnetic shielding (NICS) criteria. The resulting neutral 4N electron molecules possess a 4N π electron perimeter with pronounced CC bond length equalization (as indicated by the HOMA geometric index) and significant aromatic stabilization energies (computed using the isomerization-stabilization method) and could be promising synthetic targets with small HOMO–LUMO gaps.

Related Literature

Interactions of the intact FsrC membrane histidine kinase with the tricyclic peptideinhibitor siamycin I revealed through synchrotron radiation circular dichroism

Mary K. Phillips-Jones, Shalini Edara, Jiro Nakayama, Rohanah Hussain, Giuliano Siligardi

2012-11-14 Communication

DOI: 10.1039/C2CP43722H

Percolative proton conductivity of sol–gel derived amorphous aluminosilicate thin films

Yoshitaka Aoki, Akihisa Harada, Aiko Nakao, Toyoki Kunitake, Hiroki Habazaki

2012-01-19 Paper

DOI: 10.1039/C2CP23821G

Computational 17O-NMRspectroscopy of organic acids and peracids: comparison of solvation models

Alberto Baggioli, Orlando Crescenzi, Martin J. Field, Franca Castiglione, Guido Raos

2012-11-19 Paper

DOI: 10.1039/C2CP43021E

Exploring similarities in reactivity of superatom species: a combined theoretical and experimental investigation

Eric C. Tyo, Melanie Nöβler, Sabine Rabe, Christopher L. Harmon, Roland Mitrić, A. W. Castleman, Jr.

2011-12-19 Communication

DOI: 10.1039/C2CP23243J

Back cover

Front/Back Matter

DOI: 10.1039/C2CP90016E

Fully relativistic coupled cluster and DFT study of electric field gradients at Hg in 199Hg compounds

Vaida Arcisauskaite, Stefan Knecht, Stephan P. A. Sauer, Lars Hemmingsen

2012-01-19 Paper

DOI: 10.1039/C2CP23080A

Kinetic model for supercritical water gasification of algae

Chaohai Wei, Phillip E. Savage

2012-01-05 Paper

DOI: 10.1039/C2CP23792J

Full structural and electrochemical characterization of Li2Ti6O13 as anode for Li-ion batteries

J. C. Pérez-Flores, C. Baehtz, M. Hoelzel, A. Kuhn, F. García-Alvarado

2011-12-22 Paper

DOI: 10.1039/C2CP23741E

Contents list

Front/Back Matter

DOI: 10.1039/C2CP90011D

Photophysics of aminophenyl substituted pyrrolopyrrole cyanines

Simon Wiktorowski, Georg M. Fischer, Martin J. Winterhalder, Ewald Daltrozzo, Andreas Zumbusch

2011-12-23 Paper

DOI: 10.1039/C2CP23330D

You might also like

Compound Q&A

How should 2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) be stored?

2-Methylbenzene-1,4-diamine dihydrochloride (CAS: 615-45-2) should be stored in ...

615-45-22-Methylbenzene-1,4-...
Compound Q&A

Is (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide (CAS: 132747-20-7) safe?

(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane dihydrobromide is generally considered sa...

132747-20-7(1S,4S)-2,5-Diazabic...
Compound Q&A

What industries use (6-Chloropyridazin-3-YL)methanamine (CAS: 871826-15-2)?

(6-Chloropyridazin-3-YL)methanamine finds applications in the pharmaceutical ind...

871826-15-2(6-Chloropyridazin-3...
Compound Q&A

What are the main uses of 2-Fluoro-3-methylphenol (CAS: 77772-72-6)?

2-Fluoro-3-methylphenol is primarily used in the synthesis of pharmaceuticals, p...

77772-72-62-Fluoro-3-methylphe...
Compound Q&A

What precautions should be taken when handling 3-Methoxy-4-nitrobenzonitrile (CAS: 177476-75-4)?

When handling 3-Methoxy-4-nitrobenzonitrile, it is important to wear appropriate...

177476-75-43-Methoxy-4-nitroben...
Compound Q&A

What precautions should be taken when handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4)?

When handling 1,3-Oxazolo[4,5-b]pyridine-2(3H)-thione (CAS: 211949-57-4), it is ...

211949-57-4[1,3]Oxazolo[4,5-b]p...
Compound Q&A

What regulatory guidelines apply to 4-Ethynylbenzamide (CAS: 90347-86-7)?

4-Ethynylbenzamide (CAS: 90347-86-7) falls under various regulatory guidelines i...

90347-86-74-Ethynylbenzamide
Compound Q&A

What are the main uses of 3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone (CAS: 186822-57-1)?

3-(2-Ethylphenyl)-2-thioxo-4-imidazolidinone is primarily used as an intermediat...

186822-57-13-(2-Ethylphenyl)-2-...
Compound Q&A

What is (2-Fluoro-6-methoxyphenyl)acetic acid (CAS: 500912-19-6)?

(2-Fluoro-6-methoxyphenyl)acetic acid, also known as 4-fluoro-3-methoxybenzoic a...

500912-19-6(2-Fluoro-6-methoxyp...
Compound Q&A

What is the market or research trend for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9)?

Market trends for 2-[4-(Hydroxymethyl)phenoxy]ethanol (CAS: 102196-18-9) indicat...

102196-18-92-[4-(Hydroxymethyl)...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.