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Fluorescence Responses of the Protonation and Deprotonation Processes between Phenolate and Phenol within Rosamine
Author(s) -
Yang Ling,
Niu Jinyun,
Zhan Yanhua,
Xu Yujie,
Sun Ru,
Ge Jianfeng
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700534
Subject(s) - chemistry , protonation , deprotonation , fluorescence , titration , photochemistry , phenol , ion , hydrogen bond , inorganic chemistry , molecule , organic chemistry , physics , quantum mechanics
Two rosamine‐based pH probes 1a and 1b with pyronine‐phenol skeleton were designed and synthesized by a simple one‐step reaction. pH titration experiments showed that probes 1a and 1b exhibit near OFF–ON fluorescence responses around 550–750 nm towards the hydrogen ions. The p K a of the probe 1a is 8.29, while that of the probe 1b increases to 12.1 because of the hydrogen bond inside it. Selective and competitive experiments indicated that both common ions and amino acids did not interfere their emission with hydrogen ions. Moreover, confocal fluorescent imaging showed that the probe 1a could be served as mitochondria biomarker in HeLa and Ges‐1 cells.