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

被引：15

作者：

Tu, Ting-Hsun ^{[1
]}

Chen, Yi-Ting ^{[1
]}

Chen, Yi-An ^{[1
]}

Wei, Yu-Chen ^{[1
]}

Chen, You-Hua ^{[1
]}

Chen, Chi-Lin ^{[1
]}

Shen, Jiun-Yi ^{[1
]}

Chen, Yi-Han ^{[1
]}

Ho, Ssu-Yu ^{[1
]}

Cheng, Kum-Yi ^{[1
]}

Lee, Shern-Long ^{[1
]}

Chen, Chun-hsien ^{[1
]}

Chou, Pi-Tai ^{[1
]}

机构：

[1] Natl Taiwan Univ, Dept Chem, Taipei 10617, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 18期

关键词：

azaindole; excited-state triple proton transfer; H-bonded trimers; hydrogen bonding; self-assembly; 7-AZAINDOLE DIMER; BASE-PAIR; DYNAMICS; FLUORESCENCE; 7-AZATRYPTOPHAN; TEMPERATURE;

D O I：

10.1002/anie.201800944

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The compound 6-azaindole undergoes self-assembly by formation of N(1)-HN(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 435nm (325nm 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.

引用

页码：5020 / 5024

页数：5

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