Outside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones

Literature Information

Publication Date 2015-02-16
DOI 10.1039/C4CP05748A
Impact Factor 3.676
Authors

L. Brambilla, E. Parisini, C. Castiglioni


View Original

Abstract

The biradicaloid vs. quinoidal character of the ground state of thiophene-based heterophenoquinones bearing donor or acceptor groups is investigated. Keeping the conjugation length fixed, namely, the 5,5′-bis(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-2,2′-dihydroxy bithiophene backbone, an opposite effect occurs depending on the donating or withdrawing nature of the substituents. The character of the ground state depends not only on the electronic nature of the substituents but also on their position on the molecular skeleton: donor groups on the 3,3′-positions of the bithiophene central core stabilize a quinoidal ground state, whereas a biradicaloid electronic structure results from the introduction of the same donor groups onto the lateral phenones. Withdrawing groups behave similar to donors, but in the opposite direction.

Related Literature

A comparison of adsorbed and grafted fibronectin coatings under static and dynamic conditions

Sergio Díaz-Rodríguez, Ranna Tolouei, Pascale Chevallier, Emmanuel Pauthe, Diego Mantovani

2016-08-08 Paper

DOI: 10.1039/C6CP04527H

Utilization of the Donnan potential induced by reverse salt flux in pressure retarded osmosis systems

Chul Ho Park, Sung Jo Kwak, Joo-Youn Nam, Moon Seok Jang, Jung-Hyun Lee

2016-08-15 Communication

DOI: 10.1039/C6CP03939A

Retracted Article: Comprehensive insights into the charge dynamics process and excellent photoelectric properties of heterojunction solar cells

Xiangyang Liu, Shun Wang, Haiwu Zheng, Xiuying Cheng, Yuzong Gu

2016-07-27 Paper

DOI: 10.1039/C6CP02656G

Excitonic and vibrational coherence in artificial photosynthetic systems studied by negative-time ultrafast laser spectroscopy

Dongjia Han, Bing Xue, Juan Du, Tomohiro Miyatake, Hitoshi Tamiaki, Xin Xing, Wei Yuan, Yanyan Li

2016-08-02 Paper

DOI: 10.1039/C6CP03540J

Tuning the thermal conductivity of methylammonium lead halide by the molecular substructure

Claudia Caddeo, Claudio Melis, Maria Ilenia Saba, Alessio Filippetti, Luciano Colombo, Alessandro Mattoni

2016-07-29 Paper

DOI: 10.1039/C6CP04246E

Quantum phase transitions in Sn bilayer based interfacial systems by an external strain

Li Chen, Qiandong Zhuang, Yeqing Chen, Changmin Shi, Dongchao Wang

2016-08-03 Paper

DOI: 10.1039/C6CP04534K

Contents list

Front/Back Matter

DOI: 10.1039/C6CP90216B

A new class of N–H excited-state intramolecular proton transfer (ESIPT) molecules bearing localized zwitterionic tautomers

Anton J. Stasyuk, Yi-Ting Chen, Chi-Lin Chen, Pei-Jhen Wu, Pi-Tai Chou

2016-08-11 Paper

DOI: 10.1039/C6CP05236C

You might also like

Compound Q&A

Is 2-(2-chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) safe?

2-(2-Chloroacetamido)-3-phenylpropanoic acid (CAS: 7765-11-9) is generally consi...

7765-11-92-(2-chloroacetamido...
Compound Q&A

Is 2-(Benzyloxy)-5-bromobenzoic acid (CAS: 62176-31-2) safe?

2-(Benzyloxy)-5-bromobenzoic acid can be handled safely if appropriate precautio...

62176-31-22-(Benzyloxy)-5-brom...
Compound Q&A

What is (4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride (CAS: 1159825-48-5)?

(4-Methyl-1,2,5-oxadiazol-3-yl)methanamine hydrochloride is a chemical compound ...

1159825-48-5(4-Methyl-1,2,5-oxad...
Compound Q&A

What is 2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54-7)?

2-(5-Hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS: 917985-54...

917985-54-72-(5-Hexylthiophen-2...
Compound Q&A

Are there alternatives to 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS: 102771-26-6) in synthesis?

While 4-(8-Methyl-9H-1,3-dioxolo[4,5-h][2,3]benzodiazepin-5-yl)benzenamine (CAS:...

102771-26-64-(8-Methyl-9H-1,3-d...
Compound Q&A

What is the market or research trend for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine-6-carboxylate (CAS: 851376-80-2)?

The market for tert-butyl 3-hydroxy-4,5,7,8-tetrahydro-2H-pyrazolo[3,4-d]azepine...

851376-80-2tert-butyl 3-hydroxy...
Compound Q&A

How should waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) be handled?

Waste containing 3,5-Diamino-1H-pyrazole-4-carbonitrile (CAS: 6844-58-2) should ...

6844-58-23,5-Diamino-1H-pyraz...
Compound Q&A

How is (6-Fluoro-3-pyridinyl)boronic acid (CAS: 351019-18-6) typically synthesized?

(6-Fluoro-3-pyridinyl)boronic acid can be synthesized through the reaction of 6-...

351019-18-6(6-Fluoro-3-pyridiny...
Compound Q&A

What industries use Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9)?

Dibenzyl carbonimidoylbiscarbamate (CAS: 10065-79-9) finds applications in vario...

10065-79-9Dibenzyl carbonimido...
Compound Q&A

What is the market or research trend for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4)?

The market for (beta,beta,2,3,4,5,6-~2~H_7_)Phenylalanine (CAS: 74228-83-4) is g...

74228-83-4(beta,beta,2,3,4,5,6...

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.