biostudies-literatureUnknown12(34)West AKA 2,5-disubstituted tetrazole with <i>p</i>-nitrophenyl and 3-pyridyl units as acceptors (1a), and three push-pull tetrazoles with <i>p</i>-nitrophenyl as an acceptor and phenyl (1b), 2-(dibenzo[<i>b</i>,<i>d</i>]furan-4-yl) (1c), and 4-(<i>N</i>,<i>N</i>-diphenylamino)phenyl (1d) as donor groups, were synthesized by copper-catalyzed aerobic C-N coupling of <i>p</i>-nitrophenyl tetrazole with appropriately substituted aryl boronic acids. The absorption and emission spectra of 1a-c showed minimal dependence on the polarity of the solvent; however, in the case of 1d a blue shift was noted in the longest absorption band (<i>λ</i> ₁) as the polarity increased. The fluorescence intensity of the title compounds was found to be solvent-dependent; however, no apparent correlation to solvent polarity could be established. The absorption and emission characteristics of 1a-d were also influenced by the nature of the substituent as 1d, bearing a strong electron donating 4-(<i>N</i>,<i>N</i>-diphenylamino)phenyl group, displayed a significant red shifted absorption (<i>λ</i> ₁) as well as emission (<i>λ</i> _em) bands compared to other compounds. Time dependent density functional calculations (CAM-B3LYP/6-311++G**) revealed that the longest wavelength band (<i>λ</i> ₁) is associated with an intramolecular charge transfer (ICT) from HOMO/HOMO-1/HOMO-2 → LUMO/LUMO+1 in these molecules. The first hyperpolarizability values, <i>β</i> _HRS, of 1a-d were measured using the solution-based hyper-Rayleigh scattering technique using a femtosecond Ti:Sapphire laser and the highest NLO activity was measured for 1d with the greatest push-pull characteristics. A strong correlation was observed between the calculated hyperpolarizability (<i>β</i> _tot) and experimentally measured values (<i>β</i> _HRS).RSC advances22331-22341https://www.ebi.ac.uk/biostudies/studies/S-EPMC9364896biostudies-literatureSynthesis, photophysical and nonlinear optical properties of push-pull tetrazoles.PMC9364896Subir MWest AKRayat SKaylor LJfalseSynthesis, photophysical and nonlinear optical properties of push-pull tetrazoles.A 2,5-disubstituted tetrazole with <i>p</i>-nitrophenyl and 3-pyridyl units as acceptors (1a), and three push-pull tetrazoles with <i>p</i>-nitrophenyl as an acceptor and phenyl (1b), 2-(dibenzo[<i>b</i>,<i>d</i>]furan-4-yl) (1c), and 4-(<i>N</i>,<i>N</i>-diphenylamino)phenyl (1d) as donor groups, were synthesized by copper-catalyzed aerobic C-N coupling of <i>p</i>-nitrophenyl tetrazole with appropriately substituted aryl boronic acids. The absorption and emission spectra of 1a-c showed minimal dependence on the polarity of the solvent; however, in the case of 1d a blue shift was noted in the longest absorption band (<i>λ</i> ₁) as the polarity increased. The fluorescence intensity of the title compounds was found to be solvent-dependent; however, no apparent correlation to solvent polarity could be established. The absorption and emission characteristics of 1a-d were also influenced by the nature of the substituent as 1d, bearing a strong electron donating 4-(<i>N</i>,<i>N</i>-diphenylamino)phenyl group, displayed a significant red shifted absorption (<i>λ</i> ₁) as well as emission (<i>λ</i> _em) bands compared to other compounds. Time dependent density functional calculations (CAM-B3LYP/6-311++G**) revealed that the longest wavelength band (<i>λ</i> ₁) is associated with an intramolecular charge transfer (ICT) from HOMO/HOMO-1/HOMO-2 → LUMO/LUMO+1 in these molecules. The first hyperpolarizability values, <i>β</i> _HRS, of 1a-d were measured using the solution-based hyper-Rayleigh scattering technique using a femtosecond Ti:Sapphire laser and the highest NLO activity was measured for 1d with the greatest push-pull characteristics. A strong correlation was observed between the calculated hyperpolarizability (<i>β</i> _tot) and experimentally measured values (<i>β</i> _HRS).2022-01-01T00:00:00Z2022 Aug2025-04-18T15:24:27.376Z2025-04-07T02:00:29.312ZS-EPMC93648963604307210.1039/d2ra04307f