Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene

The chemical synthesis and physicochemical and luminescent characterizations of polymers based on 3-HT, EDOT, and 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl) bisthiophene (fluorene) or (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl 2-(thiophen-3-yl)acetate (TDR1) are reported. The fluorene u...

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Main Authors: Marco Antonio Ramírez-Gómez, Karla Karina Guzmán-Rabadán, Edgar González-Juárez, Marisol Güizado-Rodríguez, Gabriel Ramos-Ortiz, Jorge Enrique Alba-Rosales, Huehueteotl Panzo-Medrano, Victor Barba, Mario Rodríguez, José Luis Maldonado, Miguel Ángel Basurto-Pensado
Format: Article
Language:English
Published: Wiley 2017-01-01
Series:International Journal of Polymer Science
Online Access:http://dx.doi.org/10.1155/2017/1918602
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author Marco Antonio Ramírez-Gómez
Karla Karina Guzmán-Rabadán
Edgar González-Juárez
Marisol Güizado-Rodríguez
Gabriel Ramos-Ortiz
Jorge Enrique Alba-Rosales
Huehueteotl Panzo-Medrano
Victor Barba
Mario Rodríguez
José Luis Maldonado
Miguel Ángel Basurto-Pensado
author_facet Marco Antonio Ramírez-Gómez
Karla Karina Guzmán-Rabadán
Edgar González-Juárez
Marisol Güizado-Rodríguez
Gabriel Ramos-Ortiz
Jorge Enrique Alba-Rosales
Huehueteotl Panzo-Medrano
Victor Barba
Mario Rodríguez
José Luis Maldonado
Miguel Ángel Basurto-Pensado
author_sort Marco Antonio Ramírez-Gómez
collection DOAJ
description The chemical synthesis and physicochemical and luminescent characterizations of polymers based on 3-HT, EDOT, and 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl) bisthiophene (fluorene) or (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl 2-(thiophen-3-yl)acetate (TDR1) are reported. The fluorene unit was bound to the conjugate backbone, while the Disperse Red 1 (DR1) chromophore was present as a pendant group. Characterizations by 1H NMR, FT-IR, DSC-TGA, GPC, UV-vis, cyclic voltammetry, fluorescence quantum yield, excited state lifetime, and two-photon absorption cross-section were carried out. These polymers combined the physicochemical properties of EDOT and 3-HT, such as high electron density, high charge mobility, low oxidation potential, and good processability. The optical properties of these copolymers were highly dependent on the presence of EDOT, the molecular weight, and the regioregularity rather than the presence of the third component (fluorene or TDR1). The good nonlinear absorption and luminescent properties exhibited by these copolymers were exploited to fabricate nanoparticles used as fluorescent tags for the imaging of microstructures.
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spelling doaj-art-f2b3849af8a344e18843800acfebce782025-02-03T01:24:35ZengWileyInternational Journal of Polymer Science1687-94221687-94302017-01-01201710.1155/2017/19186021918602Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-EthylenedioxythiopheneMarco Antonio Ramírez-Gómez0Karla Karina Guzmán-Rabadán1Edgar González-Juárez2Marisol Güizado-Rodríguez3Gabriel Ramos-Ortiz4Jorge Enrique Alba-Rosales5Huehueteotl Panzo-Medrano6Victor Barba7Mario Rodríguez8José Luis Maldonado9Miguel Ángel Basurto-Pensado10Centro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoCentro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoCentro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoCentro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoCentro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, 37150 León, GTO, MexicoCentro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, 37150 León, GTO, MexicoCentro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, 37150 León, GTO, MexicoCentro de Investigaciones Químicas (CIQ)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoCentro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, 37150 León, GTO, MexicoCentro de Investigaciones en Óptica A.C., Loma del Bosque No. 115, Col. Lomas del Campestre, 37150 León, GTO, MexicoCentro de Investigación en Ingeniería y Ciencias Aplicadas (CIICAp)-IICBA, Universidad Autónoma del Estado de Morelos (UAEM), Av. Universidad No. 1001, Col. Chamilpa, 62209 Cuernavaca, MOR, MexicoThe chemical synthesis and physicochemical and luminescent characterizations of polymers based on 3-HT, EDOT, and 2,2′-(9,9-dioctyl-9H-fluorene-2,7-diyl) bisthiophene (fluorene) or (E)-2-(ethyl(4-((4-nitrophenyl)diazenyl)phenyl)amino)ethyl 2-(thiophen-3-yl)acetate (TDR1) are reported. The fluorene unit was bound to the conjugate backbone, while the Disperse Red 1 (DR1) chromophore was present as a pendant group. Characterizations by 1H NMR, FT-IR, DSC-TGA, GPC, UV-vis, cyclic voltammetry, fluorescence quantum yield, excited state lifetime, and two-photon absorption cross-section were carried out. These polymers combined the physicochemical properties of EDOT and 3-HT, such as high electron density, high charge mobility, low oxidation potential, and good processability. The optical properties of these copolymers were highly dependent on the presence of EDOT, the molecular weight, and the regioregularity rather than the presence of the third component (fluorene or TDR1). The good nonlinear absorption and luminescent properties exhibited by these copolymers were exploited to fabricate nanoparticles used as fluorescent tags for the imaging of microstructures.http://dx.doi.org/10.1155/2017/1918602
spellingShingle Marco Antonio Ramírez-Gómez
Karla Karina Guzmán-Rabadán
Edgar González-Juárez
Marisol Güizado-Rodríguez
Gabriel Ramos-Ortiz
Jorge Enrique Alba-Rosales
Huehueteotl Panzo-Medrano
Victor Barba
Mario Rodríguez
José Luis Maldonado
Miguel Ángel Basurto-Pensado
Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
International Journal of Polymer Science
title Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
title_full Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
title_fullStr Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
title_full_unstemmed Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
title_short Physicochemical and Luminescent Properties of Copolymers Composed of Three Monomers: Polythiophenes Based on 3-Hexylthiophene and 3,4-Ethylenedioxythiophene
title_sort physicochemical and luminescent properties of copolymers composed of three monomers polythiophenes based on 3 hexylthiophene and 3 4 ethylenedioxythiophene
url http://dx.doi.org/10.1155/2017/1918602
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