{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["12(34)"],"submitter":["West AK"],"pubmed_abstract":["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> <sub>1</sub>) 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> <sub>1</sub>) as well as emission (<i>λ</i> <sub>em</sub>) bands compared to other compounds. Time dependent density functional calculations (CAM-B3LYP/6-311++G**) revealed that the longest wavelength band (<i>λ</i> <sub>1</sub>) 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> <sub>HRS</sub>, 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> <sub>tot</sub>) and experimentally measured values (<i>β</i> <sub>HRS</sub>)."],"journal":["RSC advances"],"pagination":["22331-22341"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9364896"],"repository":["biostudies-literature"],"pubmed_title":["Synthesis, photophysical and nonlinear optical properties of push-pull tetrazoles."],"pmcid":["PMC9364896"],"pubmed_authors":["Subir M","West AK","Rayat S","Kaylor LJ"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis, photophysical and nonlinear optical properties of push-pull tetrazoles.","description":"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> <sub>1</sub>) 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> <sub>1</sub>) as well as emission (<i>λ</i> <sub>em</sub>) bands compared to other compounds. Time dependent density functional calculations (CAM-B3LYP/6-311++G**) revealed that the longest wavelength band (<i>λ</i> <sub>1</sub>) 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> <sub>HRS</sub>, 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> <sub>tot</sub>) and experimentally measured values (<i>β</i> <sub>HRS</sub>).","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Aug","modification":"2025-04-18T15:24:27.376Z","creation":"2025-04-07T02:00:29.312Z"},"accession":"S-EPMC9364896","cross_references":{"pubmed":["36043072"],"doi":["10.1039/d2ra04307f"]}}