Issue 74, 2021
From the journal:

Chemical Communications

Red fluorescent zwitterionic naphthalenediimides with di/mono-benzimidazolium and a negatively-charged oxygen substituent†

Chunqin Wang,a   Songyan Han,a   Tianbao Wang,a   Xuesong Zheng,a   Linsen Zhou,b   Yanhong Liu,a   Cheng Zhang ORCID logo a  and  Ge Gao ORCID logo *a  

* Corresponding authors

a Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China
E-mail: gg2b@scu.edu.cn

b Institute of Materials, China Academy of Engineering Physics, Mianyang 621907, P. R. China

Abstract

The C–H/C–X cross-coupling of a benzimidazolium salt with 2Br-NDI afforded two unprecedented zwitterionic NDIs with di/mono-benzimidazolium and an extra negatively-charged oxygen substituent. They exhibited intensified red fluorescence in polar solvents and negative solvatochromism due to an intramolecular charge transfer process, and could specifically label lysosomes and the endoplasmic reticulum in living A549 cells, respectively. They represent a rare case of NDI-derived ionic fluorophores.

Graphical abstract: Red fluorescent zwitterionic naphthalenediimides with di/mono-benzimidazolium and a negatively-charged oxygen substituent

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Article information

DOI
https://doi.org/10.1039/D1CC03586J
Article type
Communication
Submitted
05 Jul 2021
Accepted
16 Aug 2021
First published
16 Aug 2021

Chem. Commun., 2021,57, 9422-9425

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Red fluorescent zwitterionic naphthalenediimides with di/mono-benzimidazolium and a negatively-charged oxygen substituent

C. Wang, S. Han, T. Wang, X. Zheng, L. Zhou, Y. Liu, C. Zhang and G. Gao, Chem. Commun., 2021, 57, 9422 DOI: 10.1039/D1CC03586J

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