Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties

A series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and pphenylenediamine as π-conjugated spacers. This method was used to build...

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Authors: Hoz Ayuso, Antonio de la, Ruiz Carretero, Amparo, Noguez, O., Herrera, T., Ramírez, José Ramón, Sánchez Migallón, Ana
Format: article
Publication Date:2014
Country:España
Institution:Universidad de Castilla-La Mancha
Repository:RUIdeRA. Repositorio Institucional de la UCLM
OAI Identifier:oai:ruidera.uclm.es:10578/38635
Online Access:https://hdl.handle.net/10578/38635
Access Level:Embargoed access
Keyword:Microwave, Triazine, Optoelectronic
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spelling Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical PropertiesHoz Ayuso, Antonio de laRuiz Carretero, AmparoNoguez, O.Herrera, T.Ramírez, José RamónSánchez Migallón, AnaMicrowave, Triazine, OptoelectronicA series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and pphenylenediamine as π-conjugated spacers. This method was used to build σ−π−σ−A−σ−D systems for monotriazines and D−σ−A−σ−π−σ−A−σ−D systems for bistriazines. A study of the optoelectronic properties was performed by UV−vis and fluorescence spectroscopy and cyclic voltammetry. The monotriazines do not show any emission, but the bistriazines are blue emitters and show an interesting solvatochromic effect with large Stokes shifts of more than 10 000 cm−1 in some cases and quantum yields up to 23%. The optoelectronic properties depend on the conjugation and the position and donor character of the substituents and spacers. Cyclic voltammetry was used to determine the energy levels (HOMO and LUMO) in the bistriazines. An increase in the energy of the HOMO and a decrease in the energy of the LUMO were observed upon extending the conjugation. The title compounds showed interesting properties for use in optoelectronic devices, especially as blue emitters.ACS202420242014info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10578/38635reponame:RUIdeRA. Repositorio Institucional de la UCLMinstname:Universidad de Castilla-La ManchaInglésCTQ2011-22410/BQUinfo:eu-repo/semantics/embargoedAccessoai:ruidera.uclm.es:10578/386352026-05-27T07:36:41Z
dc.title.none.fl_str_mv Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
title Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
spellingShingle Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
Hoz Ayuso, Antonio de la
Microwave, Triazine, Optoelectronic
title_short Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
title_full Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
title_fullStr Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
title_full_unstemmed Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
title_sort Microwave Assisted Selective Synthesis of Mono and Bistriazines with Phenylenediamines as spacers. Study of their Optical Properties
dc.creator.none.fl_str_mv Hoz Ayuso, Antonio de la
Ruiz Carretero, Amparo
Noguez, O.
Herrera, T.
Ramírez, José Ramón
Sánchez Migallón, Ana
author Hoz Ayuso, Antonio de la
author_facet Hoz Ayuso, Antonio de la
Ruiz Carretero, Amparo
Noguez, O.
Herrera, T.
Ramírez, José Ramón
Sánchez Migallón, Ana
author_role author
author2 Ruiz Carretero, Amparo
Noguez, O.
Herrera, T.
Ramírez, José Ramón
Sánchez Migallón, Ana
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Microwave, Triazine, Optoelectronic
topic Microwave, Triazine, Optoelectronic
description A series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and pphenylenediamine as π-conjugated spacers. This method was used to build σ−π−σ−A−σ−D systems for monotriazines and D−σ−A−σ−π−σ−A−σ−D systems for bistriazines. A study of the optoelectronic properties was performed by UV−vis and fluorescence spectroscopy and cyclic voltammetry. The monotriazines do not show any emission, but the bistriazines are blue emitters and show an interesting solvatochromic effect with large Stokes shifts of more than 10 000 cm−1 in some cases and quantum yields up to 23%. The optoelectronic properties depend on the conjugation and the position and donor character of the substituents and spacers. Cyclic voltammetry was used to determine the energy levels (HOMO and LUMO) in the bistriazines. An increase in the energy of the HOMO and a decrease in the energy of the LUMO were observed upon extending the conjugation. The title compounds showed interesting properties for use in optoelectronic devices, especially as blue emitters.
publishDate 2014
dc.date.none.fl_str_mv 2014
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10578/38635
url https://hdl.handle.net/10578/38635
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv CTQ2011-22410/BQU
dc.rights.none.fl_str_mv info:eu-repo/semantics/embargoedAccess
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv ACS
publisher.none.fl_str_mv ACS
dc.source.none.fl_str_mv reponame:RUIdeRA. Repositorio Institucional de la UCLM
instname:Universidad de Castilla-La Mancha
instname_str Universidad de Castilla-La Mancha
reponame_str RUIdeRA. Repositorio Institucional de la UCLM
collection RUIdeRA. Repositorio Institucional de la UCLM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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