Issue 93, 2015
From the journal:

Chemical Communications

Isolation and crystal structure of a dithiophene dication: controlling covalent connection and disconnection with temperature and phase†

Ningning Yuan,a   Zaichao Zhang,b   Xingyong Wanga  and  Xinping Wang*a  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093, China
E-mail: xpwang@nju.edu.cn
Web: http://hysz.nju.edu.cn/xpwang

b School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an 223300, China

Abstract

A dithienylethene (1o) undergoes a two-electron chemical oxidation to a singlet diradical as an open-isomer (1o2+) in solution, which cyclizes to a closed-form (1c2+) upon cooling. The latter crystallizes out and its structure is analyzed by single crystal X-ray diffraction. Equilibrium between 1o2+ and 1c2+ in solution is observed by NMR and UV spectroscopy at various temperatures and is further supported by reduction reactions with Zn powder.

Graphical abstract: Isolation and crystal structure of a dithiophene dication: controlling covalent connection and disconnection with temperature and phase

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Article information

DOI
https://doi.org/10.1039/C5CC06755C
Article type
Communication
Submitted
12 Aug 2015
Accepted
24 Sep 2015
First published
24 Sep 2015

Chem. Commun., 2015,51, 16714-16717

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Isolation and crystal structure of a dithiophene dication: controlling covalent connection and disconnection with temperature and phase

N. Yuan, Z. Zhang, X. Wang and X. Wang, Chem. Commun., 2015, 51, 16714 DOI: 10.1039/C5CC06755C

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