Synthesis and photophysical properties of benzotriazole-derived unnatural α -amino acids

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, Mr Alexander and Bell, Mr Jonathan and Morgan, Mr Timaeus and Sutherland, Dr 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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
722351Sutherland ICASE 2015 (GSK)Andrew SutherlandEngineering and Physical Sciences Research Council (EPSRC)EP/N509176/1CHEM - CHEMISTRY
678901EPSRC DTG 2014Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M506539/1R&I - RESEARCH STRATEGY & INNOVATION