Bell, J. D., Morgan, T. E.F., Buijs, N., Harkiss, A. H., Wellaway, C. R. and Sutherland, A. (2019) Synthesis and photophysical properties of benzotriazole-derived unnatural α -amino acids. Journal of Organic Chemistry, 84(16), pp. 10436-10448. (doi: 10.1021/acs.joc.9b01685) (PMID:31340638)
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Abstract
The synthesis of a new class of benzotriazole-derived α-amino acid is described using a highly efficient nucleophilic aromatic substitution of ortho-fluoronitrobenzenes with l-3-aminoalanine and a polymer-supported nitrite reagent-mediated diazotization and cyclization of the subsequent 1,2-aryldiamines as the key steps. Further functionalization of the benzotriazole unit by preparation of halogenated analogues and Suzuki–Miyaura cross-coupling with aryl boronic acids allowed the synthesis of α-amino acids with conjugated side chains. Analysis of the photophysical properties of these α-amino acids revealed that incorporation of electron-rich substituents results in charge-transfer-based, fluorescent compounds with MegaStokes shifts.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Harkiss, Dr Alexander and Bell, Mr Jonathan and Morgan, Mr Timaeus and Sutherland, Professor Andrew |
| Authors: | Bell, J. D., Morgan, T. E.F., Buijs, N., Harkiss, A. H., Wellaway, C. R., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 25 July 2019 |
| Copyright Holders: | Copyright © 2019 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 84(16):10436-10448 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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