ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis, photophysical and DFT investigations on 1,2,3-triazoles linked to chalcone and chalco-pyrene

Monika Yadav, Kashmiri Lal, D. Amilan Jose, Vikas D. Ghule, and Ram Kumar Tittal

Department of Chemistry, Guru Jambheshwar University of Science & Technology, Hisar, India

E-mail: klal_iitd@yahoo.com

Received: 11 November 2022  Accepted: 18 March 2023

Abstract:

A library of chalco-pyrene linked 1,2,3-triazole hybrids containing both electron-donating and withdrawing groups were synthesized through CuAAC click chemistry and fully characterized by FTIR, ¹H-NMR, ¹³C-NMR, and HRMS data. The photophysical and DFT properties were comparatively investigated for the synthesized chalcone-linked 1,2,3-triazole. A comparative study revealed that the chalco-pyrene linked 1,2,3-triazoles are fluorescent (excimer emission in a range of 510–515 nm), while, simple chalcone linked 1,2,3-triazole (8) remained non-fluorescent due to the absence of chromophore pyrene. The emission intensity of chalco-pyrene linked alkyne 4 and 1,2,3-triazole substituted with NO₂ group i.e. 6f (1-{3-[1-(4-Nitro-benzyl)-1H-[1,2,3]triazol-4-ylmethoxy]-phenyl}-3-pyren-1-yl-propenone) is less as compared to rest of the chalco-pyrene linked 1,2,3-triazoles. The DFT study result supported and fine tuned to propose 6f as a promising semiconducting compound (least band gap of 2.95 eV and highest electrophilicity index of 6.11 eV) due to the strong electron-withdrawing nature of the –NO₂ group.

Graphical abstract

Keywords: Chalco-pyrene linked 1,2,3-triazole; CuAAC; Fluorescence; Photophysical study; DFT study

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02794-4

Chemical Papers 77 (8) 4457–4467 (2023)