Rotamer-controlled dual emissive α-amino acids

McGrory, R., Morgan, D. C., Jamieson, A. G. and Sutherland, A. (2023) Rotamer-controlled dual emissive α-amino acids. Organic Letters, 25(31), pp. 5844-5849. (doi: 10.1021/acs.orglett.3c02112) (PMID:37506290) (PMCID:PMC10425982)

Abstract

The synthesis and photoluminescent properties of novel α-amino acids are described in which the biaryl benzotriazinone-containing chromophores were found to display dual emission fluorescence via locally excited (LE) and twisted intramolecular charge transfer (TICT) states. The intensity of each emission band could be controlled by the electronics and position of the substituents, and this led to the design of a 2-methoxyphenyl analogue that, due to twisting, displayed bright TICT fluorescence, solvatochromism, and pH sensitivity.

• Item Type: Articles
• Additional Information: Financial support from the University of Glasgow (studentship to R.M.) is gratefully acknowledged.
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew and McGrory, Rochelle and Morgan, Dr Danielle and Jamieson, Professor Andrew
• Authors: McGrory, R., Morgan, D. C., Jamieson, A. G., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Organic Letters
• Publisher: American Chemical Society
• ISSN: 1523-7060
• ISSN (Online): 1523-7052
• Published Online: 28 July 2023
• Copyright Holders: Copyright © 2023 The Authors
• First Published: First published in Organic Letters 25:5844-5849
• Publisher Policy: Reproduced under a Creative Commons License