Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-Acceptor side-chain polymer and various carbazole-based H-Donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells

Duryodhan Sahu, Harihara Padhy, Dhananjaya Patra, Dhananjay Kekuda, Chih Wei Chu, I. Hung Chiang, Hong Cheu Lin

Research output: Contribution to journalArticle

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Abstract

A series of novel hydrogen-bonded (H-bonded) cross-linking polymers were generated by complexing various proton-donor (H-donor) solar cell dyes containing 3,6- and 2,7-functionalized electron-donating carbazole cores bearing symmetrical thiophene linkers and cyanoacrylic acid termini with a proton-acceptor (H-acceptor) side-chain homopolymer carrying pyridyl pendants (with 1/2 M ratio of H-donor/H-acceptor). The supramolecular H-bonded structures between H-donor dyes and the H-acceptor side-chain polymer were confirmed by FTIR measurements. The effects of the supramolecular architecture on optical, electrochemical, and organic photovoltaic (OPV) properties were investigated. From DFT (density functional theory) calculations, the optimized geometries of organic dyes reflected that the carbazole cores of H-donor dyes were coplanar with the conjugated thiophenes and cyanoacrylic acids, which is essential for strong conjugations across the donor-acceptor units in D1-D4 dyes. Under 100 mW/cm2 of AM 1.5 white-light illumination, bulk heterojunction (BHJ) OPV cell devices containing an active layer of H-bonded polymers (PDFTP/D1-D4) as an electron donor blended with [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as an electron acceptor in a weight ratio of 1:1 were explored. From the preliminary investigations, the OPV device containing 1:1 weight ratio of H-bonded polymer PDFTP/D2 and PCBM showed the best power conversion efficiency (PCE) value of 0.31% with a short-circuit current (Jsc) of 1.9 mA/cm2, an open-circuit voltage (Voc) of 0.55 V, and a fill factor (FF) of 29%, which has a higher PCE value than the corresponding H-donor D2 dye (PCE = 0.15%) or H-acceptor PDFTP homopolymer (PCE = 0.02%) blended with PCBM in 1:1 weight ratio.

Original languageEnglish
Pages (from-to)6182-6192
Number of pages11
JournalPolymer
Volume51
Issue number26
DOIs
Publication statusPublished - 10-12-2010

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Bearings (structural)
Polymers
Coloring Agents
Dyes
Hydrogen
Conversion efficiency
Acids
Thiophenes
Butyric acid
Butyric Acid
Homopolymerization
Electrons
Protons
Esters
Thiophene
Photovoltaic cells
Open circuit voltage
Short circuit currents
Density functional theory
Heterojunctions

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics

Cite this

@article{0c7887e3a33a4a7693262abad6833cef,
title = "Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-Acceptor side-chain polymer and various carbazole-based H-Donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells",
abstract = "A series of novel hydrogen-bonded (H-bonded) cross-linking polymers were generated by complexing various proton-donor (H-donor) solar cell dyes containing 3,6- and 2,7-functionalized electron-donating carbazole cores bearing symmetrical thiophene linkers and cyanoacrylic acid termini with a proton-acceptor (H-acceptor) side-chain homopolymer carrying pyridyl pendants (with 1/2 M ratio of H-donor/H-acceptor). The supramolecular H-bonded structures between H-donor dyes and the H-acceptor side-chain polymer were confirmed by FTIR measurements. The effects of the supramolecular architecture on optical, electrochemical, and organic photovoltaic (OPV) properties were investigated. From DFT (density functional theory) calculations, the optimized geometries of organic dyes reflected that the carbazole cores of H-donor dyes were coplanar with the conjugated thiophenes and cyanoacrylic acids, which is essential for strong conjugations across the donor-acceptor units in D1-D4 dyes. Under 100 mW/cm2 of AM 1.5 white-light illumination, bulk heterojunction (BHJ) OPV cell devices containing an active layer of H-bonded polymers (PDFTP/D1-D4) as an electron donor blended with [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as an electron acceptor in a weight ratio of 1:1 were explored. From the preliminary investigations, the OPV device containing 1:1 weight ratio of H-bonded polymer PDFTP/D2 and PCBM showed the best power conversion efficiency (PCE) value of 0.31{\%} with a short-circuit current (Jsc) of 1.9 mA/cm2, an open-circuit voltage (Voc) of 0.55 V, and a fill factor (FF) of 29{\%}, which has a higher PCE value than the corresponding H-donor D2 dye (PCE = 0.15{\%}) or H-acceptor PDFTP homopolymer (PCE = 0.02{\%}) blended with PCBM in 1:1 weight ratio.",
author = "Duryodhan Sahu and Harihara Padhy and Dhananjaya Patra and Dhananjay Kekuda and Chu, {Chih Wei} and Chiang, {I. Hung} and Lin, {Hong Cheu}",
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language = "English",
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Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-Acceptor side-chain polymer and various carbazole-based H-Donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells. / Sahu, Duryodhan; Padhy, Harihara; Patra, Dhananjaya; Kekuda, Dhananjay; Chu, Chih Wei; Chiang, I. Hung; Lin, Hong Cheu.

In: Polymer, Vol. 51, No. 26, 10.12.2010, p. 6182-6192.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-Acceptor side-chain polymer and various carbazole-based H-Donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells

AU - Sahu, Duryodhan

AU - Padhy, Harihara

AU - Patra, Dhananjaya

AU - Kekuda, Dhananjay

AU - Chu, Chih Wei

AU - Chiang, I. Hung

AU - Lin, Hong Cheu

PY - 2010/12/10

Y1 - 2010/12/10

N2 - A series of novel hydrogen-bonded (H-bonded) cross-linking polymers were generated by complexing various proton-donor (H-donor) solar cell dyes containing 3,6- and 2,7-functionalized electron-donating carbazole cores bearing symmetrical thiophene linkers and cyanoacrylic acid termini with a proton-acceptor (H-acceptor) side-chain homopolymer carrying pyridyl pendants (with 1/2 M ratio of H-donor/H-acceptor). The supramolecular H-bonded structures between H-donor dyes and the H-acceptor side-chain polymer were confirmed by FTIR measurements. The effects of the supramolecular architecture on optical, electrochemical, and organic photovoltaic (OPV) properties were investigated. From DFT (density functional theory) calculations, the optimized geometries of organic dyes reflected that the carbazole cores of H-donor dyes were coplanar with the conjugated thiophenes and cyanoacrylic acids, which is essential for strong conjugations across the donor-acceptor units in D1-D4 dyes. Under 100 mW/cm2 of AM 1.5 white-light illumination, bulk heterojunction (BHJ) OPV cell devices containing an active layer of H-bonded polymers (PDFTP/D1-D4) as an electron donor blended with [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as an electron acceptor in a weight ratio of 1:1 were explored. From the preliminary investigations, the OPV device containing 1:1 weight ratio of H-bonded polymer PDFTP/D2 and PCBM showed the best power conversion efficiency (PCE) value of 0.31% with a short-circuit current (Jsc) of 1.9 mA/cm2, an open-circuit voltage (Voc) of 0.55 V, and a fill factor (FF) of 29%, which has a higher PCE value than the corresponding H-donor D2 dye (PCE = 0.15%) or H-acceptor PDFTP homopolymer (PCE = 0.02%) blended with PCBM in 1:1 weight ratio.

AB - A series of novel hydrogen-bonded (H-bonded) cross-linking polymers were generated by complexing various proton-donor (H-donor) solar cell dyes containing 3,6- and 2,7-functionalized electron-donating carbazole cores bearing symmetrical thiophene linkers and cyanoacrylic acid termini with a proton-acceptor (H-acceptor) side-chain homopolymer carrying pyridyl pendants (with 1/2 M ratio of H-donor/H-acceptor). The supramolecular H-bonded structures between H-donor dyes and the H-acceptor side-chain polymer were confirmed by FTIR measurements. The effects of the supramolecular architecture on optical, electrochemical, and organic photovoltaic (OPV) properties were investigated. From DFT (density functional theory) calculations, the optimized geometries of organic dyes reflected that the carbazole cores of H-donor dyes were coplanar with the conjugated thiophenes and cyanoacrylic acids, which is essential for strong conjugations across the donor-acceptor units in D1-D4 dyes. Under 100 mW/cm2 of AM 1.5 white-light illumination, bulk heterojunction (BHJ) OPV cell devices containing an active layer of H-bonded polymers (PDFTP/D1-D4) as an electron donor blended with [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as an electron acceptor in a weight ratio of 1:1 were explored. From the preliminary investigations, the OPV device containing 1:1 weight ratio of H-bonded polymer PDFTP/D2 and PCBM showed the best power conversion efficiency (PCE) value of 0.31% with a short-circuit current (Jsc) of 1.9 mA/cm2, an open-circuit voltage (Voc) of 0.55 V, and a fill factor (FF) of 29%, which has a higher PCE value than the corresponding H-donor D2 dye (PCE = 0.15%) or H-acceptor PDFTP homopolymer (PCE = 0.02%) blended with PCBM in 1:1 weight ratio.

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