We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
The Cyclic Hydrogen‐Bonded 6‐Azaindole Trimer and its Prominent Excited‐State Triple‐Proton‐Transfer Reaction.
- Authors
Tu, Ting‐hsun; Chen, Yi‐ting; Chen, Yi‐an; Wei, Yu‐chen; Chen, You‐hua; Chen, Chi‐lin; Shen, Jiun‐yi; Chen, Yi‐han; Ho, Ssu‐yu; Cheng, Kum‐yi; Lee, Shern‐long; Chen, Chun‐hsien; Chou, Pi‐tai
- Abstract
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.
- Subjects
AZAINDOLE derivatives; HYDROGEN bonding; PROTON transfer reactions; EXCITED state chemistry; MONOMERS
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 18, p5114
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201800944