Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents

Autores
Kundu, Abhinanda; Chandra, Shubhadeep; Mandal, Debdeep; Neuman, Nicolás Ignacio; Mahata, Alok; Anga, Srinivas; Rawat, Hemant; Pal, Sudip; Schulzke, Carola; Sarkar, Biprajit; Chandrasekhar, Vadapalli; Jana, Anukul
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push-pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to a variety of substituted push-pull alkenes by varying the NHO as well as the fluoroarenes. Solid-state molecular structures of these molecules reveal a notable elongation of the central C-C bond and a twisted geometry in the alkene motif. Absorption properties were investigated with UV-vis spectroscopy. The redox properties of the twisted push-pull alkenes were probed with electrochemistry as well as UV-vis/NIR and EPR spectroelectrochemistry, while the electronic structures were computationally evaluated and validated.
Fil: Kundu, Abhinanda. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Chandra, Shubhadeep. Universitat Stuttgart; Alemania
Fil: Mandal, Debdeep. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Mahata, Alok. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Anga, Srinivas. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Rawat, Hemant. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Pal, Sudip. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);
Fil: Sarkar, Biprajit. Universität Stuttgart; Alemania
Fil: Chandrasekhar, Vadapalli. Indian Institute Of Technology Kanpur; India
Fil: Jana, Anukul. Tata Institute Of Fundamental Research, Hyderabad; India
Materia
PUSH-PULL
ALKENE
FLUORINE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/150279
Acceder
id CONICETDig_932cb13eddea8cd841e86df075a011a5
oai_identifier_str oai:ri.conicet.gov.ar:11336/150279
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl SubstituentsKundu, AbhinandaChandra, ShubhadeepMandal, DebdeepNeuman, Nicolás IgnacioMahata, AlokAnga, SrinivasRawat, HemantPal, SudipSchulzke, CarolaSarkar, BiprajitChandrasekhar, VadapalliJana, AnukulPUSH-PULLALKENEFLUORINEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push-pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to a variety of substituted push-pull alkenes by varying the NHO as well as the fluoroarenes. Solid-state molecular structures of these molecules reveal a notable elongation of the central C-C bond and a twisted geometry in the alkene motif. Absorption properties were investigated with UV-vis spectroscopy. The redox properties of the twisted push-pull alkenes were probed with electrochemistry as well as UV-vis/NIR and EPR spectroelectrochemistry, while the electronic structures were computationally evaluated and validated.Fil: Kundu, Abhinanda. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Chandra, Shubhadeep. Universitat Stuttgart; AlemaniaFil: Mandal, Debdeep. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Mahata, Alok. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Anga, Srinivas. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Rawat, Hemant. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Pal, Sudip. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; EspañaFil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);Fil: Sarkar, Biprajit. Universität Stuttgart; AlemaniaFil: Chandrasekhar, Vadapalli. Indian Institute Of Technology Kanpur; IndiaFil: Jana, Anukul. Tata Institute Of Fundamental Research, Hyderabad; IndiaAmerican Chemical Society2021-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/150279Kundu, Abhinanda; Chandra, Shubhadeep; Mandal, Debdeep; Neuman, Nicolás Ignacio; Mahata, Alok; et al.; Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents; American Chemical Society; Journal of Organic Chemistry; 86; 18; 9-2021; 12683-126920022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.1c01201info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T09:44:40Zoai:ri.conicet.gov.ar:11336/150279instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-05 09:44:41.144CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
title Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
spellingShingle Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
Kundu, Abhinanda
PUSH-PULL
ALKENE
FLUORINE
title_short Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
title_full Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
title_fullStr Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
title_full_unstemmed Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
title_sort Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
dc.creator.none.fl_str_mv Kundu, Abhinanda
Chandra, Shubhadeep
Mandal, Debdeep
Neuman, Nicolás Ignacio
Mahata, Alok
Anga, Srinivas
Rawat, Hemant
Pal, Sudip
Schulzke, Carola
Sarkar, Biprajit
Chandrasekhar, Vadapalli
Jana, Anukul
author Kundu, Abhinanda
author_facet Kundu, Abhinanda
Chandra, Shubhadeep
Mandal, Debdeep
Neuman, Nicolás Ignacio
Mahata, Alok
Anga, Srinivas
Rawat, Hemant
Pal, Sudip
Schulzke, Carola
Sarkar, Biprajit
Chandrasekhar, Vadapalli
Jana, Anukul
author_role author
author2 Chandra, Shubhadeep
Mandal, Debdeep
Neuman, Nicolás Ignacio
Mahata, Alok
Anga, Srinivas
Rawat, Hemant
Pal, Sudip
Schulzke, Carola
Sarkar, Biprajit
Chandrasekhar, Vadapalli
Jana, Anukul
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv PUSH-PULL
ALKENE
FLUORINE
topic PUSH-PULL
ALKENE
FLUORINE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push-pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to a variety of substituted push-pull alkenes by varying the NHO as well as the fluoroarenes. Solid-state molecular structures of these molecules reveal a notable elongation of the central C-C bond and a twisted geometry in the alkene motif. Absorption properties were investigated with UV-vis spectroscopy. The redox properties of the twisted push-pull alkenes were probed with electrochemistry as well as UV-vis/NIR and EPR spectroelectrochemistry, while the electronic structures were computationally evaluated and validated.
Fil: Kundu, Abhinanda. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Chandra, Shubhadeep. Universitat Stuttgart; Alemania
Fil: Mandal, Debdeep. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Neuman, Nicolás Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Mahata, Alok. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Anga, Srinivas. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Rawat, Hemant. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Pal, Sudip. International Centre Of Theoretical Science. Tata Institute Of Fundamental Research; España
Fil: Schulzke, Carola. ERNST MORITZ ARNDT UNIVERSITÄT GREIFSWALD (UG);
Fil: Sarkar, Biprajit. Universität Stuttgart; Alemania
Fil: Chandrasekhar, Vadapalli. Indian Institute Of Technology Kanpur; India
Fil: Jana, Anukul. Tata Institute Of Fundamental Research, Hyderabad; India
description The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push-pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to a variety of substituted push-pull alkenes by varying the NHO as well as the fluoroarenes. Solid-state molecular structures of these molecules reveal a notable elongation of the central C-C bond and a twisted geometry in the alkene motif. Absorption properties were investigated with UV-vis spectroscopy. The redox properties of the twisted push-pull alkenes were probed with electrochemistry as well as UV-vis/NIR and EPR spectroelectrochemistry, while the electronic structures were computationally evaluated and validated.
publishDate 2021
dc.date.none.fl_str_mv 2021-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/150279
Kundu, Abhinanda; Chandra, Shubhadeep; Mandal, Debdeep; Neuman, Nicolás Ignacio; Mahata, Alok; et al.; Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents; American Chemical Society; Journal of Organic Chemistry; 86; 18; 9-2021; 12683-12692
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/150279
identifier_str_mv Kundu, Abhinanda; Chandra, Shubhadeep; Mandal, Debdeep; Neuman, Nicolás Ignacio; Mahata, Alok; et al.; Twisted Push-Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents; American Chemical Society; Journal of Organic Chemistry; 86; 18; 9-2021; 12683-12692
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.1c01201
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1847977061709250560
score 13.087074

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