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. 2023 Aug 11;25(31):5844-5849.
doi: 10.1021/acs.orglett.3c02112. Epub 2023 Jul 28.

Rotamer-Controlled Dual Emissive α-Amino Acids

Rochelle McGrory  1 , Danielle C Morgan  2 , Andrew G Jamieson  2 , Andrew Sutherland  1
Affiliations

Rotamer-Controlled Dual Emissive α-Amino Acids

Rochelle McGrory et al. Org Lett. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Fluorescent unnatural α-amino acids.
Scheme 1
Scheme 1. Proposed Synthesis of Benzotriazinone Amino Acids
Scheme 2
Scheme 2. Synthesis of α-Amino Acids 10a–e
Figure 2
Figure 2
Emission spectra of α-amino acids 10a–e.
Figure 3
Figure 3
(a) Emission spectra of 10e in various solvents. (b) Emission spectra of 10e at pH 1, 4, and 7. All spectra were recorded by using a concentration of 5 μM.
Scheme 3
Scheme 3. Reversible Acidic Triazinone Ring-Opening of 10e
Scheme 4
Scheme 4. SPPS Synthesis of Dodecapeptide 12
See this image and copyright information in PMC

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