title: Asymmetric Donor-π-Acceptor-Type Benzo-Fused Aza-BODIPYs: Facile Synthesis and Colorimetric Properties.
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 B-N 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 B-N bond cleavage may disrupt the whole π-conjugation of the BODIPY molecule, resulting in significant colorimetric behavior.
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Wei
authors.initials: W
authors.lastname: Zheng
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Bei-Bei
authors.initials: BB
authors.lastname: Wang
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China). chli@nju.edu.cn.
authors.forename: Cheng-Hui
authors.initials: CH
authors.lastname: Li
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Jing-Xuan
authors.initials: JX
authors.lastname: Zhang
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Cheng-Zhang
authors.initials: CZ
authors.lastname: Wan
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Jia-Hao
authors.initials: JH
authors.lastname: Huang
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China).
authors.forename: Jian
authors.initials: J
authors.lastname: Liu
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China). zshen@nju.edu.cn.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Shen
authors.affiliation: State Key laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing 210093 (P. R. China). youxz@nju.edu.cn.
authors.forename: Xiao-Zeng
authors.initials: XZ
authors.lastname: You
keywords: CH activation; aza-BODIPY; colorimetry; dyes