Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group

A new series of bent-core molecules containing a photoactive π-conjugated structure (azobenzene, stilbene or cyanostilbene) linked to the central aromatic ring by an amide group was synthesized and characterized. Their liquid crystalline properties were analyzed in relation to the molecular structur...

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Autores: Simić, Kristina Gak, Đorđević, Ivana, Rybak, Paulina, Pociecha, Damian, Giménez, Raquel, Ros, M. Blanca, Trišović, Nemanja P.
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2026
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/425145
Acesso em linha:http://hdl.handle.net/10261/425145
Access Level:acceso embargado
Palavra-chave:Bent-core liquid crystals
Aggregation-induced emission
Mechanofluorochromism
Conformational analysis
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spelling Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking groupSimić, Kristina GakĐorđević, IvanaRybak, PaulinaPociecha, DamianGiménez, RaquelRos, M. BlancaTrišović, Nemanja P.Bent-core liquid crystalsAggregation-induced emissionMechanofluorochromismConformational analysisA new series of bent-core molecules containing a photoactive π-conjugated structure (azobenzene, stilbene or cyanostilbene) linked to the central aromatic ring by an amide group was synthesized and characterized. Their liquid crystalline properties were analyzed in relation to the molecular structure and compared with amide-containing bent-core liquid crystals from the literature. Replacement of the azobenzene structure with a unit based on stilbene, either with or without a cyano substituent, accounted for the most significant differences in liquid crystalline behavior among the synthesized compounds. Azobenzene compound exhibited an enantiotropic B7-type phase, while (cyano)stilbene compounds formed a monotropic B1Rev phase. Cyanostilbene derivatives were fluorescent and showed aggregation-induced emission (AIE) enhancement. Furthermore, these compounds showed mechanofluorochromism, as observable emission changes in the solid state as a result of mechanical grinding. These changes turned to be reversible upon fuming with tetrahydrofuran vapor. Quantum-chemical calculations were employed to provide a detailed analysis of the most probable conformers, the impact of the cyano group orientation on the transverse and longitudinal components of the molecular dipole moment, and the electronic properties. The obtained results offer valuable molecular design guidelines for the development of new stimuli-responsive self-assembled materials.This research was funded by the Ministry of Science, Technological Development, and Innovation of the Republic of Serbia (Grants Nos. 451-03-136/2025-03/200026, 451-03-136/2025-03/200135 and 451-03-136/2025-03/200287), the Spanish project PID2021-122882NB-I00 financed by MCIN/AEI/10.13039/501100011033/ and by “ERDF A way of making Europe” and the INMA Severo Ochoa Excellence Center CEX2023-001286-S 564 grant financed by MCIU/AEI/10.13039/501100011033/, and the Gobierno de Aragón/FEDER (research group E47_23R). INMA authors' would like to acknowledge the thermal analysis service of CEQMA (CSIC-Universidad de Zaragoza). This research follows the United Nations 2030 Agenda for Sustainable Development Goal (SDG) 9: Industry, Innovation and Infrastructure.With funding from the Spanish government through the "Severo Ochoa Centre of Excellence" accreditation (CEX2023-001286-S).Peer reviewedElsevierMinistry of Science, Technological Development and Innovation (Serbia)Ministerio de Ciencia, Innovación y Universidades (España)Agencia Estatal de Investigación (España)European CommissionGobierno de AragónConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202620262026info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10261/425145reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-122882NB-I00info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/CEX2023-001286-SSimić, Kristina Gak; Đorđević, Ivana; Rybak, Paulina; Pociecha, Damian; Giménez, Raquel; Ros, M. Blanca; Trišović, Nemanja P.; 2026; Appendix A. Supplementary data of Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group [Dataset]; Elsevier; https://doi.org/10.1016/j.molliq.2025.129175https://doi.org/10.1016/j.molliq.2025.129175Síinfo:eu-repo/semantics/embargoedAccessoai:digital.csic.es:10261/4251452026-05-22T06:33:51Z
dc.title.none.fl_str_mv Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
title Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
spellingShingle Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
Simić, Kristina Gak
Bent-core liquid crystals
Aggregation-induced emission
Mechanofluorochromism
Conformational analysis
title_short Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
title_full Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
title_fullStr Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
title_full_unstemmed Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
title_sort Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group
dc.creator.none.fl_str_mv Simić, Kristina Gak
Đorđević, Ivana
Rybak, Paulina
Pociecha, Damian
Giménez, Raquel
Ros, M. Blanca
Trišović, Nemanja P.
author Simić, Kristina Gak
author_facet Simić, Kristina Gak
Đorđević, Ivana
Rybak, Paulina
Pociecha, Damian
Giménez, Raquel
Ros, M. Blanca
Trišović, Nemanja P.
author_role author
author2 Đorđević, Ivana
Rybak, Paulina
Pociecha, Damian
Giménez, Raquel
Ros, M. Blanca
Trišović, Nemanja P.
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministry of Science, Technological Development and Innovation (Serbia)
Ministerio de Ciencia, Innovación y Universidades (España)
Agencia Estatal de Investigación (España)
European Commission
Gobierno de Aragón
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Bent-core liquid crystals
Aggregation-induced emission
Mechanofluorochromism
Conformational analysis
topic Bent-core liquid crystals
Aggregation-induced emission
Mechanofluorochromism
Conformational analysis
description A new series of bent-core molecules containing a photoactive π-conjugated structure (azobenzene, stilbene or cyanostilbene) linked to the central aromatic ring by an amide group was synthesized and characterized. Their liquid crystalline properties were analyzed in relation to the molecular structure and compared with amide-containing bent-core liquid crystals from the literature. Replacement of the azobenzene structure with a unit based on stilbene, either with or without a cyano substituent, accounted for the most significant differences in liquid crystalline behavior among the synthesized compounds. Azobenzene compound exhibited an enantiotropic B7-type phase, while (cyano)stilbene compounds formed a monotropic B1Rev phase. Cyanostilbene derivatives were fluorescent and showed aggregation-induced emission (AIE) enhancement. Furthermore, these compounds showed mechanofluorochromism, as observable emission changes in the solid state as a result of mechanical grinding. These changes turned to be reversible upon fuming with tetrahydrofuran vapor. Quantum-chemical calculations were employed to provide a detailed analysis of the most probable conformers, the impact of the cyano group orientation on the transverse and longitudinal components of the molecular dipole moment, and the electronic properties. The obtained results offer valuable molecular design guidelines for the development of new stimuli-responsive self-assembled materials.
publishDate 2026
dc.date.none.fl_str_mv 2026
2026
2026
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/425145
url http://hdl.handle.net/10261/425145
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-122882NB-I00
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/CEX2023-001286-S
Simić, Kristina Gak; Đorđević, Ivana; Rybak, Paulina; Pociecha, Damian; Giménez, Raquel; Ros, M. Blanca; Trišović, Nemanja P.; 2026; Appendix A. Supplementary data of Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group [Dataset]; Elsevier; https://doi.org/10.1016/j.molliq.2025.129175
https://doi.org/10.1016/j.molliq.2025.129175
Sí
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 Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
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