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- Title
Asymmetric Donor-π-Acceptor-Type Benzo-Fused Aza-BODIPYs: Facile Synthesis and Colorimetric Properties.
- Authors
Zheng, Wei; Wang, Bei-Bei; Li, Cheng-Hui; Zhang, Jing-Xuan; Wan, Cheng-Zhang; Huang, Jia-Hao; Liu, Jian; Shen, Zhen; You, Xiao-Zeng
- Abstract
Novel aza-diisoindolylmethene and their BF2-chelating complexes (benzo-fused aza-BODIPYs) were synthesized on a large scale and in a facile manner from phthalonitrile in tBuOK-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 1H and 11B 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.
- Subjects
AZA compounds; COLORIMETRY; BENZENEDICARBONITRILE; SOLUTION (Chemistry); TRIFLUOROACETIC acid
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 31, p9198
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201501984