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The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone

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Abstract

1,3-Dipolar cycloaddition of pyrido[2,1-a]isoindole with internal alkynes functionalized by a BMes2ph and an N-aromatic heterocycle leads to the formation of two types of regioisomers (major a and minor b) that have distinct physical and photophysical properties. Examination on 5 pairs of regioisomers unveils that the major isomers consistently have a smaller optical energy gap and emission energy than the corresponding minor isomers, which is greatly amplified by the formation of an internal B ← N bond. The regioisomers with a B ← N bond display contrasting temperature-dependent structural dynamics and response to fluoride ions, owing to an entropy-driven or fluoride initiated B ← N bond rupture/ring-opening process and the different B ← N bond strength. The opposite inductive effect and the Lewis pair properties of the dichotomic substituent units are responsible for the contrasting properties of the regioisomers in this system.

Graphical abstract: The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone

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Publication details

The article was received on 21 Sep 2018, accepted on 27 Nov 2018 and first published on 29 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC04210A
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    The opposite and amplifying effect of B ← N coordination on photophysical properties of regioisomers with an unsymmetrical backbone

    C. Zeng, K. Yuan, N. Wang, T. Peng, G. Wu and S. Wang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04210A

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