Cargando…
Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design
Polyazomethines containing electron-donor triphenylamine (TPA) or carbazole (Cbz) and electron-acceptor naphthyl(di)imide were synthesized and investigated with regard to thermal, optical and electronic features, with a focus on their modulation by molecular design. The polycondesation of an imido-b...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504240/ https://www.ncbi.nlm.nih.gov/pubmed/36144497 http://dx.doi.org/10.3390/molecules27185761 |
_version_ | 1784796166205997056 |
---|---|
author | Soroceanu, Marius Constantin, Catalin-Paul Damaceanu, Mariana-Dana |
author_facet | Soroceanu, Marius Constantin, Catalin-Paul Damaceanu, Mariana-Dana |
author_sort | Soroceanu, Marius |
collection | PubMed |
description | Polyazomethines containing electron-donor triphenylamine (TPA) or carbazole (Cbz) and electron-acceptor naphthyl(di)imide were synthesized and investigated with regard to thermal, optical and electronic features, with a focus on their modulation by molecular design. The polycondesation of an imido-based diamine with a Cbz- or TPA-based dialdehyde led to donor-acceptor polymers with good thermostability, up to 318 °C. These displayed good solubility in organic solvents, which enabled easy polymer processability in thin films with different molecular assemblies. The molecular order improved the charge carrier’s mobility, with a direct impact on the bandgap energy. The optical properties studied by UV–Vis absorption and fluorescence experiments showed solvent-dependence, characteristic for donor-acceptor systems. The structural parameters exerted a strong influence on the light-emissive behavior, with the prevalence of intrinsic or intramolecular charge transfer fluorescence contingent on the donor-acceptor strength and polymer geometry. All polymers showed good electroactivity, supporting both electrons and holes transport. The exchange of Cbz with TPA proved to be an efficient tool with which to decrease the bandgap energy, while that of naphthyl(di)imide with bis(naphthylimide) was beneficial for fluorescence enhancement. This study may contribute to a deeper understanding of the physico-chemistry of electronic materials so as to make them more competitive in the newest energy-related or other optoelectronic devices. |
format | Online Article Text |
id | pubmed-9504240 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-95042402022-09-24 Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design Soroceanu, Marius Constantin, Catalin-Paul Damaceanu, Mariana-Dana Molecules Article Polyazomethines containing electron-donor triphenylamine (TPA) or carbazole (Cbz) and electron-acceptor naphthyl(di)imide were synthesized and investigated with regard to thermal, optical and electronic features, with a focus on their modulation by molecular design. The polycondesation of an imido-based diamine with a Cbz- or TPA-based dialdehyde led to donor-acceptor polymers with good thermostability, up to 318 °C. These displayed good solubility in organic solvents, which enabled easy polymer processability in thin films with different molecular assemblies. The molecular order improved the charge carrier’s mobility, with a direct impact on the bandgap energy. The optical properties studied by UV–Vis absorption and fluorescence experiments showed solvent-dependence, characteristic for donor-acceptor systems. The structural parameters exerted a strong influence on the light-emissive behavior, with the prevalence of intrinsic or intramolecular charge transfer fluorescence contingent on the donor-acceptor strength and polymer geometry. All polymers showed good electroactivity, supporting both electrons and holes transport. The exchange of Cbz with TPA proved to be an efficient tool with which to decrease the bandgap energy, while that of naphthyl(di)imide with bis(naphthylimide) was beneficial for fluorescence enhancement. This study may contribute to a deeper understanding of the physico-chemistry of electronic materials so as to make them more competitive in the newest energy-related or other optoelectronic devices. MDPI 2022-09-06 /pmc/articles/PMC9504240/ /pubmed/36144497 http://dx.doi.org/10.3390/molecules27185761 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Soroceanu, Marius Constantin, Catalin-Paul Damaceanu, Mariana-Dana Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title | Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title_full | Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title_fullStr | Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title_full_unstemmed | Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title_short | Polynaphthylimide–Azomethines Containing Triphenylamine or Carbazole Moieties with Tuned Optoelectronic Properties through Molecular Design |
title_sort | polynaphthylimide–azomethines containing triphenylamine or carbazole moieties with tuned optoelectronic properties through molecular design |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9504240/ https://www.ncbi.nlm.nih.gov/pubmed/36144497 http://dx.doi.org/10.3390/molecules27185761 |
work_keys_str_mv | AT soroceanumarius polynaphthylimideazomethinescontainingtriphenylamineorcarbazolemoietieswithtunedoptoelectronicpropertiesthroughmoleculardesign AT constantincatalinpaul polynaphthylimideazomethinescontainingtriphenylamineorcarbazolemoietieswithtunedoptoelectronicpropertiesthroughmoleculardesign AT damaceanumarianadana polynaphthylimideazomethinescontainingtriphenylamineorcarbazolemoietieswithtunedoptoelectronicpropertiesthroughmoleculardesign |