The Cyclic Hydrogen-Bonded 6-Azaindole Trimer and its Prominent Excited-State Triple-Proton-Transfer Reaction

Angewandte Chemie
Ting-Hsun TuPi-Tai Chou

Abstract

The compound 6-azaindole undergoes self-assembly by formation of N(1)-H⋅⋅⋅N(6) hydrogen bonds (H bonds), forming a cyclic, triply H-bonded trimer. The formation phenomenon is visualized by scanning tunneling microscopy. Remarkably, the H-bonded trimer undergoes excited-state triple proton transfer (ESTPT), resulting in a proton-transfer tautomer emission maximized at 435 nm (325 nm of the normal emission) in cyclohexane. Computational approaches affirm the thermodynamically favorable H-bonded trimer formation and the associated ESTPT reaction. Thus, nearly half a century after Michael Kasha discovered the double H-bonded dimer of 7-azaindole and its associated excited-state double-proton-transfer reaction, the triply H-bonded trimer formation of 6-azaindole and its ESTPT reaction are demonstrated.

References

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Nov 2, 2013·Nature Communications·Jiun-Yi ShenPi-Tai Chou
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Feb 13, 2015·The Journal of Physical Chemistry. B·Pi-Tai Chou, Kyril M Solntsev

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Citations

Aug 14, 2020·Physical Chemistry Chemical Physics : PCCP·Iker LamasLluís Blancafort
Oct 20, 2018·Physical Chemistry Chemical Physics : PCCP·Saugata SahuG Krishnamoorthy
Jun 16, 2018·Accounts of Chemical Research·Panwang Zhou, Keli Han

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