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Fluorescent 1‐Arylidene‐1,3‐dihydroisobenzofuran: Ligand‐Free Palladium Nanoparticles, Catalyzed Domino Synthesis and Photophysical Studies
Author(s) -
Mandali Pavan Kumar,
Pati Avik Kumar,
Mishra Ashok Kumar,
Chand Dillip Kumar
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700730
Subject(s) - sonogashira coupling , intramolecular force , photochemistry , palladium , cyclohexane , chemistry , excited state , fluorescence , ligand (biochemistry) , acetonitrile , combinatorial chemistry , catalysis , stereochemistry , organic chemistry , receptor , biochemistry , physics , quantum mechanics , nuclear physics
The present work describes synthesis and photophysical studies of a class of fluorophores containing biologically relevant 1,3‐dihydroisobenzofuran scaffold. Ligand‐free palladium nanoparticles have been utilized for domino synthesis of 1‐arylidene‐1,3‐dihydroisobenzofurans from 2‐iodobenzyl alcohol and terminal arylacetylenes under mild reaction conditions. Reaction of terminal alkylacetylenes with 2‐iodobenzyl alcohol however, provided only the Sonogashira products (2‐(alk‐1‐ynyl)phenyl)methanols. The 1‐arylidene‐1,3‐dihydroisobenzofuran derivatives showed structured fluorescence spectra in non‐polar cyclohexane, originated from a locally excited state and structureless emission in polar acetonitrile involving intramolecular charge transfer process. The vibronic structures in the locally excited emission were confined to the ring C=C stretching of the dyes. A detailed structure‐property relationship of the 1‐arylidene‐1,3‐dihydroisobenzofuran dyes is presented in this study.