Pyrrolo[1,2-a]quinoxaline: A Combined Experimental and Computational Study on the Photophysical Properties of a New Photofunctional Building Block DOI Creative Commons
Adarash Kumar Shukla,

Savita Choudhary,

Dilawar Singh Sisodiya

и другие.

The Journal of Physical Chemistry B, Год журнала: 2025, Номер unknown

Опубликована: Июнь 1, 2025

We report a detailed photophysical exploration of medicinally important pyrrolo[1,2-a]quinoxalines. Pyrrolo[1,2-a]quinoxaline (QHH), 2,4-diphenylpyrrolo[1,2-a]quinoxaline (QPP), 2-phenyl-4-(thiophen-2-yl)pyrrolo[1,2-a]quinoxaline (QPT), and 4-phenyl-2-(thiophen-2-yl)pyrrolo[1,2-a]quinoxaline (QTP) were synthesized studied using various techniques. Preliminary studies revealed the environmental responsiveness these systems along with involvement aggregation-induced emission (AIE). Molecules QPP QTP displayed significant fluorescence enhancement via AIE when compared to QHH QPT. The fluorophores could be used for bioimaging subcellular localization, specifically on lysosomes. TDDFT that both S0-S1 S0-S2 transitions dominate higher-wavelength peaks in absorption spectra nonrigid PQNs. A complete charge delocalization was seen fluorescent S1 state rigid unsubstituted analogue. In contrast, its 2,4-disubstituted analogues, electronic clouds benzene thiophene rings adjacent fused pyrrole PQN moieties absent. states latter molecules undergo ISC higher triplets (T2/T3) through further twisting C-C bonds, accompanied by high transfer 1.5- 3.0-fold increase dipole moments. These identified as phosphorescent states, while triplet T1 seems responsible ROS generation, aided aggregation. Computational results validated phosphorescence studies, which showed lowest intensity completely QHH, highest observed case QPP. Subsequent also generation capability systems, indicated computational results. This work establishes versatility pyrrolo[1,2-a]quinoxaline core puts forward plausible mechanism features.

Язык: Английский

Pyrrolo[1,2-a]quinoxaline: A Combined Experimental and Computational Study on the Photophysical Properties of a New Photofunctional Building Block DOI Creative Commons
Adarash Kumar Shukla,

Savita Choudhary,

Dilawar Singh Sisodiya

и другие.

The Journal of Physical Chemistry B, Год журнала: 2025, Номер unknown

Опубликована: Июнь 1, 2025

We report a detailed photophysical exploration of medicinally important pyrrolo[1,2-a]quinoxalines. Pyrrolo[1,2-a]quinoxaline (QHH), 2,4-diphenylpyrrolo[1,2-a]quinoxaline (QPP), 2-phenyl-4-(thiophen-2-yl)pyrrolo[1,2-a]quinoxaline (QPT), and 4-phenyl-2-(thiophen-2-yl)pyrrolo[1,2-a]quinoxaline (QTP) were synthesized studied using various techniques. Preliminary studies revealed the environmental responsiveness these systems along with involvement aggregation-induced emission (AIE). Molecules QPP QTP displayed significant fluorescence enhancement via AIE when compared to QHH QPT. The fluorophores could be used for bioimaging subcellular localization, specifically on lysosomes. TDDFT that both S0-S1 S0-S2 transitions dominate higher-wavelength peaks in absorption spectra nonrigid PQNs. A complete charge delocalization was seen fluorescent S1 state rigid unsubstituted analogue. In contrast, its 2,4-disubstituted analogues, electronic clouds benzene thiophene rings adjacent fused pyrrole PQN moieties absent. states latter molecules undergo ISC higher triplets (T2/T3) through further twisting C-C bonds, accompanied by high transfer 1.5- 3.0-fold increase dipole moments. These identified as phosphorescent states, while triplet T1 seems responsible ROS generation, aided aggregation. Computational results validated phosphorescence studies, which showed lowest intensity completely QHH, highest observed case QPP. Subsequent also generation capability systems, indicated computational results. This work establishes versatility pyrrolo[1,2-a]quinoxaline core puts forward plausible mechanism features.

Язык: Английский

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