2022
DOI: 10.3390/molecules27206879
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Synthesis and Photophysical Properties of α-(N-Biphenyl)-Substituted 2,2′-Bipyridine-Based Push–Pull Fluorophores

Abstract: A series of new α-(N-biphenyl)-substituted 2,2′-bipyridines were obtained through the combination of the ipso-nucleophilic aromatic substitution of the C5-cyano group, aza-Diels–Alder and Suzuki cross-coupling reactions, starting from 5-cyano-1,2,4-triazines. For the obtained compounds, photophysical and fluorosolvatochromic properties were studied. Fluorophores 3l and 3b demonstrated unexpected AIEE activity, while 3a and 3h showed promising nitroexplosive detection abilities.

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Cited by 8 publications
(3 citation statements)
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“…Hydrogen bonds could assist in the formation of complexes of pyridine containing compounds 2tCzPy, 3tCzPy, and 4tCzPy with chloroform inducing further geometrical structural changes in the molecules as previously reported for pyridine containing compounds. 40 It should be noted that the emission of chloroform solutions of the studied compounds resulted not only from CT between phenylpyridine and di-tertbutyl-carbazole moieties but also from the complexes of the compounds with chloroform (Fig. 3(d)-(f)).…”
Section: Photophysical Propertiesmentioning
confidence: 91%
“…Hydrogen bonds could assist in the formation of complexes of pyridine containing compounds 2tCzPy, 3tCzPy, and 4tCzPy with chloroform inducing further geometrical structural changes in the molecules as previously reported for pyridine containing compounds. 40 It should be noted that the emission of chloroform solutions of the studied compounds resulted not only from CT between phenylpyridine and di-tertbutyl-carbazole moieties but also from the complexes of the compounds with chloroform (Fig. 3(d)-(f)).…”
Section: Photophysical Propertiesmentioning
confidence: 91%
“…The density functional theory (DFT) was conducted using the B3LYP/6-31G (d) level of theory with the Gaussian 09 program. The graphical outputs of the computational results were then generated using Multiwfn software 68 and VMD – visual molecular dynamics software.…”
Section: Methodsmentioning
confidence: 99%
“…Furthermore, the correlation between the Stokes shift and the empirical solvent polarity parameter E T (30) also helps to confirm the solvent-dependent effect. 67,68 The empirical polarity parameter E T (30) was proposed by Reichardt, which is an empirical parameter used to characterize solvent polarity with a specified compound as a standard. 69 It is applicable to various polar solvents.…”
Section: Solvatochromismmentioning
confidence: 99%