Structural tuning of β-enamino diketones: exploration of solution and crystalline state photochromism

Kiran B Manjappa; Sheng-Chieh Fan; Ding-Yah Yang

doi:10.3389/fchem.2023.1295347

Structural tuning of β-enamino diketones: exploration of solution and crystalline state photochromism

Front Chem. 2023 Nov 7:11:1295347. doi: 10.3389/fchem.2023.1295347. eCollection 2023.

Authors

Kiran B Manjappa¹, Sheng-Chieh Fan², Ding-Yah Yang^{1

2}

Affiliations

¹ Graduate Program for Biomedical and Materials Science, Tunghai University, Taichung, Taiwan.
² Department of Chemistry, Tunghai University, Taichung, Taiwan.

Abstract

A library of β-enamino diketones was prepared via base-mediated, three-component reaction of 4-hydroxycoumarins with various aromatic/aliphatic amines and β-nitrostyrenes under microwave irradiation conditions to investigate their photochemical properties. Among the prepared compounds, a thiophene derived β-enamino diketone was found to be light-sensitive and to exhibit unique photochromic behavior, that is, positive photochromism in solution and negative photochromism in crystalline phase. In addition, this prepared photochromic compound was further covalently linked to a structure-related, piezochromic β-enamino diketone moiety to explore its potential multi-stimuli responsive properties.

Keywords: functional property; microwave; multi-responsive; photochromism; photosensitive; piezochromism; thiophene; β-enamino diketones.

Grants and funding

The author(s) declare financial support was received for the research, authorship, and/or publication of this article. National Science and Technology Council of Taiwan Contract No. NSTC 109-2113-M-029-010-MY3 (DYY) and 108-2113-M-029-004 (KBM).