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Updated: Oct 20, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Red fluorescent zwitterionic naphthalenediimides with di/mono-benzimidazolium and a negatively-charged oxygen
Chunqin Wang1, Songyan Han1, Tianbao Wang1
1Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China. gg2b@scu.edu.cn.
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.
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