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1 H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1 H ‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis
Author(s) -
Anandhan Karnambaram,
Cerón Margarita,
Ceballos Paulina,
RamosHernández Rodrigo,
Perumal Venkatesan,
PérezGutiérrez Enrique,
SosaRivadeneyra Martha,
Thamotharan Subbiah,
Percino M. Judith
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904505
Subject(s) - benzaldehyde , chemistry , natural bond orbital , intermolecular force , fluorescence , analytical chemistry (journal) , orthorhombic crystal system , crystallography , proton nmr , absorption (acoustics) , density functional theory , crystal structure , photochemistry , molecule , stereochemistry , computational chemistry , materials science , organic chemistry , physics , quantum mechanics , catalysis , composite material
Abstract In the present study the molecular structure of compound 4‐(4,5‐diphenyl‐1 H ‐imidazol‐2‐yl)benzaldehyde [ DPI‐BA ] and its optoelectronic properties are reported. The SCXRD analysis revealed that DPI‐BA crystallizes in the Orthorhombic crystal system and P ca2 1 space group with Z=4. The intermolecular N‐H⋅⋅N interaction generates a one‐dimensional chain. An interesting halochromic behavior was observed for the DPI‐BA in THF:H 2 O (9:1) by varying the pH analysis. The fluorescence properties of neutral and acid‐base solutions were monitored by UV‐vis and 1D, 2D‐NMR studies. The HCl vapor was bubbled to the DPI‐BA in the DMSO‐d6 solution and the corresponding fluorescence wavelength changed from green (λ em 501 nm) to blue (λ em 459 nm). In the case of a basic pH solution was made by adding NaOH flakes to the DPI‐BA DMSO‐d6 solution and then the fluorescence wavelength changed from green to orange (λ em 595 nm). The λ max of PL emission could be correlated to intermolecular charge transfer (ICT). The optical absorption and cyclic voltammetry measurement were performed to determine the bandgap. Besides, the quantitative analysis of intermolecular interactions through PIXEL, QTAIM, NBO, GIAO‐DFT methods and DFT studies was correlated to the experiments.