Issue 88, 2017, Issue in Progress

An acidic pH fluorescent probe based on Tröger's base


A novel pH fluorescent probe 2,8-(6H,12H-5,11-methanodibenzo[b,f]diazocineylene)-di(p-ethenyl-pyridine) (TBPP) incorporating an electron-donating amine moiety and electron-accepting pyridine group through Tröger's base linker was designed and synthesized. TBPP exhibits an intramolecular charge transfer effect caused by the donor–acceptor interaction between its amine and pyridine units. Its emission can be reversibly switched between blue and dark states by protonation and deprotonation. Such behavior enables it to work as a turn-off fluorescent pH sensor in solution state. 1H NMR spectroscopy analysis suggests that the change in electron affinity of the pyridinyl unit upon protonation and deprotonation is responsible for such sensing processes.

Graphical abstract: An acidic pH fluorescent probe based on Tröger's base

Article information

Article type
12 Oct 2017
02 Dec 2017
First published
07 Dec 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 55577-55581

An acidic pH fluorescent probe based on Tröger's base

C. Yuan, Y. Zhang, H. Xi and X. Tao, RSC Adv., 2017, 7, 55577 DOI: 10.1039/C7RA11228A

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