Broadening the absorption of conjugated polymers by "click" functionalization with phthalocyanines

Bert J. Campo; Jan Duchateau; Carolina R. Ganivet; Beatriz Ballesteros; Jan Gilot; Martijn M. Wienk; Wibren D. Oosterbaan; Laurence Lutsen; Thomas J. Cleij; Gema de la Torre; Rene A. J. Janssen; Dirk Vanderzande; Tomas Torres

doi:10.1039/c0dt01348j

Broadening the absorption of conjugated polymers by "click" functionalization with phthalocyanines

Bert J. Campo^*, Jan Duchateau, Carolina R. Ganivet, Beatriz Ballesteros, Jan Gilot, Martijn M. Wienk, Wibren D. Oosterbaan, Laurence Lutsen, Thomas J. Cleij, Gema de la Torre, Rene A. J. Janssen, Dirk Vanderzande, Tomas Torres

^*Corresponding author for this work

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

29 Citations (Web of Science)

Abstract

Conjugated copolymer derivatives of poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV) and poly(3-hexylthiophene) (P3HT) containing 10% of alkyne functionalities in the side chains have been prepared using the sulfinyl precursor route and the Rieke method, respectively. With the aim of expanding the absorption range of these conjugated polymers for their use in bulk heterojunction (BHJ) polymer:fullerene solar cells, appropriate phthalocyanine (Pc) molecules have been covalently bound through a post-polymerization "click chemistry" reaction between the alkyne functionalities in the side chains of the copolymers and a Pc functionalized with an azide moiety. The resulting poly(p-phenylenevinylene)-Pc (PPV-Pc) material holds a 9 mol% content of Pcs, while the polythiophene-Pc material (PT-Pc) contains a 8 mol% of Pc-functionalization in the side chains. As expected, the presence of the Pc contributes to the extension of the absorption up to 700 nm. BHJ solar cells have been prepared using PPV-Pc and PT-Pc materials in combination with PCBM. Although the Pc absorption contributes to the generation of photocurrent, the overall power conversion efficiencies (PCE) obtained from these cells are lower than those obtained with BHJ P3HT:PCBM (1:1) and MDMO-PPV:PCBM (1:4) solar cells. A plausible explanation could be the moderate solubility of the PPV-Pc and PT-Pc materials that limits the processing into thin films.

Original language	English
Pages (from-to)	3979-3988
Journal	Dalton Transactions
Volume	40
Issue number	15
DOIs	https://doi.org/10.1039/c0dt01348j
Publication status	Published - 2011
Externally published	Yes

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Campo, B. J., Duchateau, J., Ganivet, C. R., Ballesteros, B., Gilot, J., Wienk, M. M., Oosterbaan, W. D., Lutsen, L., Cleij, T. J., de la Torre, G., Janssen, R. A. J., Vanderzande, D., & Torres, T. (2011). Broadening the absorption of conjugated polymers by "click" functionalization with phthalocyanines. Dalton Transactions, 40(15), 3979-3988. https://doi.org/10.1039/c0dt01348j

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title = "Broadening the absorption of conjugated polymers by {"}click{"} functionalization with phthalocyanines",

abstract = "Conjugated copolymer derivatives of poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV) and poly(3-hexylthiophene) (P3HT) containing 10% of alkyne functionalities in the side chains have been prepared using the sulfinyl precursor route and the Rieke method, respectively. With the aim of expanding the absorption range of these conjugated polymers for their use in bulk heterojunction (BHJ) polymer:fullerene solar cells, appropriate phthalocyanine (Pc) molecules have been covalently bound through a post-polymerization {"}click chemistry{"} reaction between the alkyne functionalities in the side chains of the copolymers and a Pc functionalized with an azide moiety. The resulting poly(p-phenylenevinylene)-Pc (PPV-Pc) material holds a 9 mol% content of Pcs, while the polythiophene-Pc material (PT-Pc) contains a 8 mol% of Pc-functionalization in the side chains. As expected, the presence of the Pc contributes to the extension of the absorption up to 700 nm. BHJ solar cells have been prepared using PPV-Pc and PT-Pc materials in combination with PCBM. Although the Pc absorption contributes to the generation of photocurrent, the overall power conversion efficiencies (PCE) obtained from these cells are lower than those obtained with BHJ P3HT:PCBM (1:1) and MDMO-PPV:PCBM (1:4) solar cells. A plausible explanation could be the moderate solubility of the PPV-Pc and PT-Pc materials that limits the processing into thin films.",

author = "Campo, {Bert J.} and Jan Duchateau and Ganivet, {Carolina R.} and Beatriz Ballesteros and Jan Gilot and Wienk, {Martijn M.} and Oosterbaan, {Wibren D.} and Laurence Lutsen and Cleij, {Thomas J.} and {de la Torre}, Gema and Janssen, {Rene A. J.} and Dirk Vanderzande and Tomas Torres",

year = "2011",

doi = "10.1039/c0dt01348j",

language = "English",

volume = "40",

pages = "3979--3988",

journal = "Dalton Transactions",

issn = "1477-9226",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Broadening the absorption of conjugated polymers by "click" functionalization with phthalocyanines

AU - Campo, Bert J.

AU - Duchateau, Jan

AU - Ganivet, Carolina R.

AU - Ballesteros, Beatriz

AU - Gilot, Jan

AU - Wienk, Martijn M.

AU - Oosterbaan, Wibren D.

AU - Lutsen, Laurence

AU - Cleij, Thomas J.

AU - de la Torre, Gema

AU - Janssen, Rene A. J.

AU - Vanderzande, Dirk

AU - Torres, Tomas

PY - 2011

Y1 - 2011

N2 - Conjugated copolymer derivatives of poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV) and poly(3-hexylthiophene) (P3HT) containing 10% of alkyne functionalities in the side chains have been prepared using the sulfinyl precursor route and the Rieke method, respectively. With the aim of expanding the absorption range of these conjugated polymers for their use in bulk heterojunction (BHJ) polymer:fullerene solar cells, appropriate phthalocyanine (Pc) molecules have been covalently bound through a post-polymerization "click chemistry" reaction between the alkyne functionalities in the side chains of the copolymers and a Pc functionalized with an azide moiety. The resulting poly(p-phenylenevinylene)-Pc (PPV-Pc) material holds a 9 mol% content of Pcs, while the polythiophene-Pc material (PT-Pc) contains a 8 mol% of Pc-functionalization in the side chains. As expected, the presence of the Pc contributes to the extension of the absorption up to 700 nm. BHJ solar cells have been prepared using PPV-Pc and PT-Pc materials in combination with PCBM. Although the Pc absorption contributes to the generation of photocurrent, the overall power conversion efficiencies (PCE) obtained from these cells are lower than those obtained with BHJ P3HT:PCBM (1:1) and MDMO-PPV:PCBM (1:4) solar cells. A plausible explanation could be the moderate solubility of the PPV-Pc and PT-Pc materials that limits the processing into thin films.

AB - Conjugated copolymer derivatives of poly[2-methoxy-5-(3',7'-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV) and poly(3-hexylthiophene) (P3HT) containing 10% of alkyne functionalities in the side chains have been prepared using the sulfinyl precursor route and the Rieke method, respectively. With the aim of expanding the absorption range of these conjugated polymers for their use in bulk heterojunction (BHJ) polymer:fullerene solar cells, appropriate phthalocyanine (Pc) molecules have been covalently bound through a post-polymerization "click chemistry" reaction between the alkyne functionalities in the side chains of the copolymers and a Pc functionalized with an azide moiety. The resulting poly(p-phenylenevinylene)-Pc (PPV-Pc) material holds a 9 mol% content of Pcs, while the polythiophene-Pc material (PT-Pc) contains a 8 mol% of Pc-functionalization in the side chains. As expected, the presence of the Pc contributes to the extension of the absorption up to 700 nm. BHJ solar cells have been prepared using PPV-Pc and PT-Pc materials in combination with PCBM. Although the Pc absorption contributes to the generation of photocurrent, the overall power conversion efficiencies (PCE) obtained from these cells are lower than those obtained with BHJ P3HT:PCBM (1:1) and MDMO-PPV:PCBM (1:4) solar cells. A plausible explanation could be the moderate solubility of the PPV-Pc and PT-Pc materials that limits the processing into thin films.

U2 - 10.1039/c0dt01348j

DO - 10.1039/c0dt01348j

M3 - Article

C2 - 21416102

VL - 40

SP - 3979

EP - 3988

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 15

ER -