Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties

Vivian Suru John; Vera Cimrova; Christoph Ulbricht; Veronika Pokorna; Ales Ruzicka; Jean-Benoit Giguere; Antoine Lafleur-Lambert; Jean-Francois Morin; Emmanuel Iwuoha; Daniel Ayuk Mbi Egbe

doi:10.1021/acs.macromol.7b02136

Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties

Vivian Suru John, Vera Cimrova, Christoph Ulbricht, Veronika Pokorna, Ales Ruzicka, Jean-Benoit Giguere, Antoine Lafleur-Lambert, Jean-Francois Morin, Emmanuel Iwuoha, Daniel Ayuk Mbi Egbe

Institute of Polymeric Materials and Testing

Research output: Contribution to journal › Article › peer-review

Abstract

ABSTRACT: Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1−P5) based on poly[(arylene ethynylene)-alt- (arylene vinylene)]s backbone (−Ph−CC−Anth−CC− Ph−CHCH−Ph−CHCH−)n. During the synthesis of P1−P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2- ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1−P3 are reported, compared and discussed with respect to the effects of side chains.

Original language	English
Pages (from-to)	8357-8371
Number of pages	15
Journal	Macromolecules
Volume	50 (21)
DOIs	https://doi.org/10.1021/acs.macromol.7b02136
Publication status	Published - Nov 2017

Fields of science

205 Materials Engineering
205011 Polymer engineering
205016 Materials testing
207106 Renewable energy
211908 Energy research
103023 Polymer physics
104018 Polymer chemistry
211909 Energy technology
104019 Polymer sciences

JKU Focus areas

Nano-, Bio- and Polymer-Systems: From Structure to Function

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.macromol.7b02136

Cite this

John, V. S., Cimrova, V., Ulbricht, C., Pokorna, V., Ruzicka, A., Giguere, J.-B., Lafleur-Lambert, A., Morin, J.-F., Iwuoha, E., & Egbe, D. A. M. (2017). Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties. Macromolecules, 50 (21), 8357-8371. https://doi.org/10.1021/acs.macromol.7b02136

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title = "Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties",

abstract = "ABSTRACT: Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1−P5) based on poly[(arylene ethynylene)-alt- (arylene vinylene)]s backbone (−Ph−CC−Anth−CC− Ph−CHCH−Ph−CHCH−)n. During the synthesis of P1−P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2- ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1−P3 are reported, compared and discussed with respect to the effects of side chains.",

author = "John, \{Vivian Suru\} and Vera Cimrova and Christoph Ulbricht and Veronika Pokorna and Ales Ruzicka and Jean-Benoit Giguere and Antoine Lafleur-Lambert and Jean-Francois Morin and Emmanuel Iwuoha and Egbe, \{Daniel Ayuk Mbi\}",

year = "2017",

month = nov,

doi = "10.1021/acs.macromol.7b02136",

language = "English",

volume = "50 (21)",

pages = "8357--8371",

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John, VS, Cimrova, V, Ulbricht, C, Pokorna, V, Ruzicka, A, Giguere, J-B, Lafleur-Lambert, A, Morin, J-F, Iwuoha, E & Egbe, DAM 2017, 'Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties', Macromolecules, vol. 50 (21), pp. 8357-8371. https://doi.org/10.1021/acs.macromol.7b02136

Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties. / John, Vivian Suru; Cimrova, Vera; Ulbricht, Christoph et al.
In: Macromolecules, Vol. 50 (21), 11.2017, p. 8357-8371.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Poly[(arylene ethynylene)-alt-(arylene vinylene)]s Based on Anthanthrone and Its Derivatives: Synthesis and Photophysical, Electrochemical, Electroluminescent, and Photovoltaic Properties

AU - John, Vivian Suru

AU - Cimrova, Vera

AU - Ulbricht, Christoph

AU - Pokorna, Veronika

AU - Ruzicka, Ales

AU - Giguere, Jean-Benoit

AU - Lafleur-Lambert, Antoine

AU - Morin, Jean-Francois

AU - Iwuoha, Emmanuel

AU - Egbe, Daniel Ayuk Mbi

PY - 2017/11

Y1 - 2017/11

N2 - ABSTRACT: Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1−P5) based on poly[(arylene ethynylene)-alt- (arylene vinylene)]s backbone (−Ph−CC−Anth−CC− Ph−CHCH−Ph−CHCH−)n. During the synthesis of P1−P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2- ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1−P3 are reported, compared and discussed with respect to the effects of side chains.

AB - ABSTRACT: Anthanthrone and its derivatives are large polycyclic aromatic compounds (PACs) that pose a number of challenges for incorporation into the structure of soluble conjugated polymers. For the first time, this group of PACs was employed as the building blocks for the synthesis of copolymers (P1−P5) based on poly[(arylene ethynylene)-alt- (arylene vinylene)]s backbone (−Ph−CC−Anth−CC− Ph−CHCH−Ph−CHCH−)n. During the synthesis of P1−P5, different alkyloxy side chains were incorporated in order to tune the properties of the polymers. Of the copolymer series only P1 (containing anthanthrone and branched 2- ethylhexyloxy side chains on phenylenes), P2 and P3 (for which the anthanthrones containing carbonyl groups were converted to anthanthrene containing alkyloxy substituents) were soluble. The photophysical, electrochemical, electroluminescent and photovoltaic properties of P1−P3 are reported, compared and discussed with respect to the effects of side chains.

U2 - 10.1021/acs.macromol.7b02136

DO - 10.1021/acs.macromol.7b02136

M3 - Article

SN - 0024-9297

VL - 50 (21)

SP - 8357

EP - 8371

JO - Macromolecules

JF - Macromolecules

ER -