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Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules
Perylene diimide (PDI) is one of the most studied functional dyes due to their structural versatility and fine tuning of the materials properties. Core substituted PDIs are prominent n-type semiconductor materials that could be used as non-fullerene acceptors in organic photovoltaics. Herein, we dev...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930630/ https://www.ncbi.nlm.nih.gov/pubmed/31810324 http://dx.doi.org/10.3390/molecules24234406 |
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author | Aivali, Stefania Tsimpouki, Loukia Anastasopoulos, Charalampos Kallitsis, Joannis K. |
author_facet | Aivali, Stefania Tsimpouki, Loukia Anastasopoulos, Charalampos Kallitsis, Joannis K. |
author_sort | Aivali, Stefania |
collection | PubMed |
description | Perylene diimide (PDI) is one of the most studied functional dyes due to their structural versatility and fine tuning of the materials properties. Core substituted PDIs are prominent n-type semiconductor materials that could be used as non-fullerene acceptors in organic photovoltaics. Herein, we develop versatile organic building blocks based on PDI by decorating the PDI core with quinoline groups. Styryl and hydroxy phenyl mono and difunctionalized molecules were prepared using mono-nitro and dibromo bay substituted PDIs by Suzuki coupling with the respective boronic acid derivatives. A novel methodology using nitro-PDI under Suzuki coupling conditions as an electrophile partner was successfully tested. Furthermore, the PDI derivatives were used for the synthesis of soluble, electron accepting small molecules combining PDI with weak electron withdrawing quinoline derivatives. The new molecules presented wide absorbance in the visible spectrum from 450 to almost 700 nm while their LUMO levels and their energy levels are in the range of −3.8 to −4.2 eV. |
format | Online Article Text |
id | pubmed-6930630 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-69306302019-12-26 Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules Aivali, Stefania Tsimpouki, Loukia Anastasopoulos, Charalampos Kallitsis, Joannis K. Molecules Article Perylene diimide (PDI) is one of the most studied functional dyes due to their structural versatility and fine tuning of the materials properties. Core substituted PDIs are prominent n-type semiconductor materials that could be used as non-fullerene acceptors in organic photovoltaics. Herein, we develop versatile organic building blocks based on PDI by decorating the PDI core with quinoline groups. Styryl and hydroxy phenyl mono and difunctionalized molecules were prepared using mono-nitro and dibromo bay substituted PDIs by Suzuki coupling with the respective boronic acid derivatives. A novel methodology using nitro-PDI under Suzuki coupling conditions as an electrophile partner was successfully tested. Furthermore, the PDI derivatives were used for the synthesis of soluble, electron accepting small molecules combining PDI with weak electron withdrawing quinoline derivatives. The new molecules presented wide absorbance in the visible spectrum from 450 to almost 700 nm while their LUMO levels and their energy levels are in the range of −3.8 to −4.2 eV. MDPI 2019-12-02 /pmc/articles/PMC6930630/ /pubmed/31810324 http://dx.doi.org/10.3390/molecules24234406 Text en © 2019 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Aivali, Stefania Tsimpouki, Loukia Anastasopoulos, Charalampos Kallitsis, Joannis K. Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title | Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title_full | Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title_fullStr | Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title_full_unstemmed | Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title_short | Synthesis and Optoelectronic Characterization of Perylene Diimide-Quinoline Based Small Molecules |
title_sort | synthesis and optoelectronic characterization of perylene diimide-quinoline based small molecules |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6930630/ https://www.ncbi.nlm.nih.gov/pubmed/31810324 http://dx.doi.org/10.3390/molecules24234406 |
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