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Dual Colorimetric/Fluorometric Double‐Throw pH‐Switches: The Dimroth Rearrangement of N , 9 ‐Diaryl 8‐Azaadenines
Author(s) -
Li Bo,
Jiang Shichao,
Gao Jingshuo,
Wu Xueting,
Deng Jiajie,
Zhang Linmeng,
Yu Zhipeng
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900117
Subject(s) - chemistry , acridine , nucleobase , molecule , mass spectrometry , molecular switch , aryl , combinatorial chemistry , stereochemistry , chromatography , organic chemistry , dna , biochemistry , alkyl
A library of 12 N , 9 ‐Diaryl 2‐methyl‐8‐azaadenine (DAMA) compounds was designed and constructed through an aryl‐pairing combination strategy for identifying a nucleobase‐containing molecular switch that functions by the pH‐regulated Dimroth rearrangement. By utilizing 2D thin‐layer chromatography/mass spectrometry (2D‐TLC‐MS), the DAMA compounds were easily screened to identify which compounds could be used as molecular switches. The pH‐switching ability of the DAMA was achieved by incorporating the acridine group as the key structural unit, as well as dual‐modal colorimetric/fluorometric on/off properties as the probe functions. The real‐time tracing of the switching process clearly indicated that the paired aromatics on both terminals of the DAMA molecule play a key role in tuning the switching kinetics.