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Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds

Pyrazine derivatives quinoxaline and pyridopyrazine were selected as the acceptors, and benzocarbazole was used as the donor to synthesize four different D–A–D compounds. The results showed that 2,3-bis(decyloxy)pyridine[3,4-b]pyrazine (DPP) exhibited stronger electron-withdrawing ability than that...

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Autores principales: Song, Xuejing, Kong, Lingqian, Du, Hongmei, Li, Xiangyu, Feng, Hanlin, Zhao, Jinsheng, Xie, Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6213557/
https://www.ncbi.nlm.nih.gov/pubmed/30360424
http://dx.doi.org/10.3390/ma11102063
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author Song, Xuejing
Kong, Lingqian
Du, Hongmei
Li, Xiangyu
Feng, Hanlin
Zhao, Jinsheng
Xie, Yu
author_facet Song, Xuejing
Kong, Lingqian
Du, Hongmei
Li, Xiangyu
Feng, Hanlin
Zhao, Jinsheng
Xie, Yu
author_sort Song, Xuejing
collection PubMed
description Pyrazine derivatives quinoxaline and pyridopyrazine were selected as the acceptors, and benzocarbazole was used as the donor to synthesize four different D–A–D compounds. The results showed that 2,3-bis(decyloxy)pyridine[3,4-b]pyrazine (DPP) exhibited stronger electron-withdrawing ability than that of 2,3-bis(decyloxy)quinoxaline (DPx), because DPP possesses one more nitrogen (N) atom, resulting in a red-shift of the intramolecular charge transfer (ICT) absorption bands and fluorescent emission spectra for compounds with DPP as the acceptor compared with those that use DPx as the acceptor. The band-gap energy (Eg) of the four D–A–D compounds were 2.82 eV, 2.70 eV, 2.48 eV, and 2.62 eV, respectively, for BPC-2DPx, BPC-3DPx, BPC-2DPP, and BPC-3DPP. The solvatochromic effect was insignificant when the four compounds were in the ground state, which became significant in an excited state. With increasing solvent polarity, a 30–43 nm red shift was observed in the emissive spectra of the compounds. The thermal decomposition temperatures of the four compounds between 436 and 453 °C had very high thermal stability. Resistor-type memory devices based on BPC-2DPx and BPC-2DPP were fabricated in a simple sandwich configuration, Al/BPC-2DPx/ITO or Al/BPC-2DPP/ITO. The two devices showed a binary non-volatile flash memory, with lower threshold voltages and better repeatability.
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spelling pubmed-62135572018-11-14 Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds Song, Xuejing Kong, Lingqian Du, Hongmei Li, Xiangyu Feng, Hanlin Zhao, Jinsheng Xie, Yu Materials (Basel) Article Pyrazine derivatives quinoxaline and pyridopyrazine were selected as the acceptors, and benzocarbazole was used as the donor to synthesize four different D–A–D compounds. The results showed that 2,3-bis(decyloxy)pyridine[3,4-b]pyrazine (DPP) exhibited stronger electron-withdrawing ability than that of 2,3-bis(decyloxy)quinoxaline (DPx), because DPP possesses one more nitrogen (N) atom, resulting in a red-shift of the intramolecular charge transfer (ICT) absorption bands and fluorescent emission spectra for compounds with DPP as the acceptor compared with those that use DPx as the acceptor. The band-gap energy (Eg) of the four D–A–D compounds were 2.82 eV, 2.70 eV, 2.48 eV, and 2.62 eV, respectively, for BPC-2DPx, BPC-3DPx, BPC-2DPP, and BPC-3DPP. The solvatochromic effect was insignificant when the four compounds were in the ground state, which became significant in an excited state. With increasing solvent polarity, a 30–43 nm red shift was observed in the emissive spectra of the compounds. The thermal decomposition temperatures of the four compounds between 436 and 453 °C had very high thermal stability. Resistor-type memory devices based on BPC-2DPx and BPC-2DPP were fabricated in a simple sandwich configuration, Al/BPC-2DPx/ITO or Al/BPC-2DPP/ITO. The two devices showed a binary non-volatile flash memory, with lower threshold voltages and better repeatability. MDPI 2018-10-22 /pmc/articles/PMC6213557/ /pubmed/30360424 http://dx.doi.org/10.3390/ma11102063 Text en © 2018 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
Song, Xuejing
Kong, Lingqian
Du, Hongmei
Li, Xiangyu
Feng, Hanlin
Zhao, Jinsheng
Xie, Yu
Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title_full Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title_fullStr Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title_full_unstemmed Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title_short Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds
title_sort effects of pyrazine derivatives and substituted positions on the photoelectric properties and electromemory performance of d–a–d series compounds
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6213557/
https://www.ncbi.nlm.nih.gov/pubmed/30360424
http://dx.doi.org/10.3390/ma11102063
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