In the present work, we report the chemical synthesis of a newly π-conjugated system using a Wittig reaction. The chemical structure of the synthesized molecule named 1,4-Bis((E)-2-(1-methyl-pyrrol-2-yl)vinyl)benzene (BisPyrBz) was supported by Fourier transform infrared spectroscopy. The optical properties were investigated first using optical absorption (O.A) and steady-state photoluminescence (PLs) tools. Otherwise, transient photoluminescence (TRPL) and quantum yield measurements (PLQY) are present in a diluted solution and condensed state. Theoretical investigations on the synthesized molecule were performed using density functional density (DFT). Experimental and theoretical data show the formation of a planar π-conjugated system. The obtained molecule presents a blue emission with high PLQY, at around 35 % in the solution state. The emission is red-shifted to the green color, with a drastic decrease of the PLQY to around 1 % indicating a possible aggregation-caused quenching behavior in the condensed state. The use of the synthesized BisPyrBz as a π linker in a newly designed A-π-D small molecule permits to obtain a newly near-infrared absorbing material with a weak energy gap Eg = ELUMO − EHOMO, which is at around 1.93 eV, and a weak optical band gap which is estimated to be 1.67 eV.

Experimental and theoretical investigations on the photophysical and electronic properties of new synthesized organic small molecule for optoelectronic applications / M. Chemek, M. Ben Braiek, I. Rosenbusch, F. Rizzo, N. Wazzan, A. Hafiane, K. Alimi. - In: OPTICAL MATERIALS. - ISSN 0925-3467. - 157:(2024 Nov), pp. 116104.1-116104.10. [10.1016/j.optmat.2024.116104]

Experimental and theoretical investigations on the photophysical and electronic properties of new synthesized organic small molecule for optoelectronic applications

F. Rizzo;
2024

Abstract

In the present work, we report the chemical synthesis of a newly π-conjugated system using a Wittig reaction. The chemical structure of the synthesized molecule named 1,4-Bis((E)-2-(1-methyl-pyrrol-2-yl)vinyl)benzene (BisPyrBz) was supported by Fourier transform infrared spectroscopy. The optical properties were investigated first using optical absorption (O.A) and steady-state photoluminescence (PLs) tools. Otherwise, transient photoluminescence (TRPL) and quantum yield measurements (PLQY) are present in a diluted solution and condensed state. Theoretical investigations on the synthesized molecule were performed using density functional density (DFT). Experimental and theoretical data show the formation of a planar π-conjugated system. The obtained molecule presents a blue emission with high PLQY, at around 35 % in the solution state. The emission is red-shifted to the green color, with a drastic decrease of the PLQY to around 1 % indicating a possible aggregation-caused quenching behavior in the condensed state. The use of the synthesized BisPyrBz as a π linker in a newly designed A-π-D small molecule permits to obtain a newly near-infrared absorbing material with a weak energy gap Eg = ELUMO − EHOMO, which is at around 1.93 eV, and a weak optical band gap which is estimated to be 1.67 eV.
Density functional density (DFT); Dye; Optical absorption (O.A); Steady-state photoluminescence (PL); π-conjugated system;
Settore CHEM-05/A - Chimica organica
Settore CHEM-05/A - Chimica organica
nov-2024
https://www.sciencedirect.com/science/article/abs/pii/S0925346724012874
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1104749
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