Uncovering and controlling the ESIPT behavior for 2, 2‐dipicolylamino substituted 2‐(2′‐hydroxybenzofuranyl) benzoxazole: Solvent polarity. (5th October 2022)

• Record Type: Journal Article
• Authors: Zhao, Jinfeng; Fan, Liming; Feng, Lu; Jin, Bing; Zhao, Shutao
• Is Part Of: Journal of physical organic chemistry. Volume 36:Number 2(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-05
• Subjects: charge transfer -- ESIPT -- frontier molecular orbital -- hydrogen bond; Chemistry, Physical organic -- Periodicals; 547.1
• DOI: 10.1002/poc.4440
• Languages: English
• ISSNs: 0894-3230

Abstract

Abstract: In view of potential applications of fluorescent probe for the novel 2, 2‐dipicolylamino substituted 2‐(2′‐hydroxybenzofuranyl) benzoxazole (HBBODipic) dye, herein, we mainly focus on exploring effect of solvent polarity on ESIPT behavior for HBBODipoc. First, we compare the dominating atomic charge distribution, geometric parameters, and infrared (IR) vibrational behaviors of HBBODipic, and we confirm that intramolecular hydrogen bond O–H···N could be strengthened in S1 state and nonpolar solvents are more conducive to the strengthening of hydrogen bonds. Via studying frontier molecular orbitals (MOs), we clarify that intramolecular charge transfer (ICT) occurs in excited molecule and charge redistribution facilitates ESIPT for HBBODipoc. In particular, nonpolar solvent is more propitious to ESIPT process of HBBODipic. Finally, we calculate and compare the potential energy curve of HBBODipic in solvent with different polarities. We present that the ESIPT process of HBBODipic could be regulated by solvent polarity; that is, nonpolar solvents are more favorable for ESIPT reaction for HBBODipic flurophore. Abstract : S1 ‐state enhancement of hydrogen bond of HBBODipic facilitates ESIPT process. Photo‐induced ICT and charge redistribution facilitate ESIPT reaction. The nonpolar solvent polarity can contribute to promote ESIPT behavior for HBBODipic fluorophore.