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Asymmetric Donor–π‐Acceptor‐Type Benzo‐Fused Aza‐BODIPYs: Facile Synthesis and Colorimetric Properties
Author(s) -
Zheng Wei,
Wang BeiBei,
Li ChengHui,
Zhang JingXuan,
Wan ChengZhang,
Huang JiaHao,
Liu Jian,
Shen Zhen,
You XiaoZeng
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501984
Subject(s) - hypsochromic shift , chemistry , trifluoroacetic acid , dichloromethane , photochemistry , acceptor , molecule , triple bond , density functional theory , fluorescence , polymer chemistry , organic chemistry , double bond , computational chemistry , solvent , physics , quantum mechanics , condensed matter physics
Novel aza‐diisoindolylmethene and their BF 2 ‐chelating complexes (benzo‐fused aza‐BODIPYs) were synthesized on a large scale and in a facile manner from phthalonitrile in t BuOK‐DMF solution. The unique asymmetric donor–π‐acceptor structure facilitates BN bond detachment in the presence of trifluoroacetic acid (TFA) in dichloromethane, resulting in sharp color change from red to colorless, with over 250 nm hypsochromic shift in the absorption maximum. This colorimetric process can be reversed by adding a very small amount of proton‐accepting solvents or compounds. A 1 H and 11 B NMR spectroscopy study and also density functional theory (DFT) calculations suggest that TFA‐induced BN bond cleavage may disrupt the whole π‐conjugation of the BODIPY molecule, resulting in significant colorimetric behavior.