Impact of Terminal End-Group of Acceptor-Donor-Acceptor-type Small Molecules on Molecular Packing and Photovoltaic Properties

Sang Woo Kim; Yu Jeong Lee; Young Woong Lee; Chang Woo Koh; Yeran Lee; Min Je Kim; Kin Liao; Jeong Ho Cho; Bumjoon J. Kim; Han Young Woo

doi:10.1021/acsami.8b13928

Impact of Terminal End-Group of Acceptor-Donor-Acceptor-type Small Molecules on Molecular Packing and Photovoltaic Properties

Sang Woo Kim, Yu Jeong Lee, Young Woong Lee, Chang Woo Koh, Yeran Lee, Min Je Kim, Kin Liao, Jeong Ho Cho, Bumjoon J. Kim, Han Young Woo

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

19 Citations (Scopus)

Abstract

In this study, we synthesized two acceptor-donor-acceptor (A-D-A)-type small molecules (SMs) (P3T4-VCN and P3T4-INCN) with different terminal end-groups (dicyanovinyl (VCN) and 2-methylene-3-(1,1-dicyanomethylene)indanone (INCN)) based on the 1,4-bis(thiophenylphenylthiophene)-2,5-difluorophenylene (P3T4) core that possesses high coplanarity because of intrachain noncovalent Coulombic interactions. We investigated the influence of terminal end-groups on intermolecular packing and the resulting electrical and photovoltaic characteristics. A small change in the end-group structure of the SMs induces a significant variation in the torsional structures, molecular packing, and pristine/blend film morphology. It is noteworthy that the less crystalline P3T4-INCN with tilted conformation is highly sensitive to post-treatments (i.e., additives and annealing) such that it permits facile morphological modulation. However, the highly planar and crystalline P3T4-VCN exhibits a strong tolerance toward processing treatments. After morphology optimization, the fullerene-based bulk-heterojunction solar cell of tilted P3T4-INCN exhibits a power conversion efficiency (PCE) of 5.68%, which is significantly superior to that of P3T4-VCN:PC₇₁BM (PCE = 1.29%). Our results demonstrate the importance of the terminal end-group for the design of A-D-A-type SMs and their sensitivity toward the postprocessing treatments in optimizing their performance.

Original language	English
Pages (from-to)	39952-39961
Number of pages	10
Journal	ACS Applied Materials and Interfaces
Volume	10
Issue number	46
DOIs	https://doi.org/10.1021/acsami.8b13928
Publication status	Published - 2018 Nov 21

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation (NRF) of Korea (Grants NRF-2016M1A2A2940911, 2017K2A9A2A12000315, 2015M1A2A2057506, and 2015R1D1A1A09056905). We acknowledge additional support for this work from the Research Projects of the KAIST-KUSTAR.

Publisher Copyright:
Copyright © 2018 American Chemical Society.

Keywords

A-D-A structure
Coulombic interaction
molecular planarity
organic solar cell
post-treatment

ASJC Scopus subject areas

General Materials Science

UN SDGs

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

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@article{6a0d8bb629254d1b9d2c39f7db81cf76,

title = "Impact of Terminal End-Group of Acceptor-Donor-Acceptor-type Small Molecules on Molecular Packing and Photovoltaic Properties",

abstract = "In this study, we synthesized two acceptor-donor-acceptor (A-D-A)-type small molecules (SMs) (P3T4-VCN and P3T4-INCN) with different terminal end-groups (dicyanovinyl (VCN) and 2-methylene-3-(1,1-dicyanomethylene)indanone (INCN)) based on the 1,4-bis(thiophenylphenylthiophene)-2,5-difluorophenylene (P3T4) core that possesses high coplanarity because of intrachain noncovalent Coulombic interactions. We investigated the influence of terminal end-groups on intermolecular packing and the resulting electrical and photovoltaic characteristics. A small change in the end-group structure of the SMs induces a significant variation in the torsional structures, molecular packing, and pristine/blend film morphology. It is noteworthy that the less crystalline P3T4-INCN with tilted conformation is highly sensitive to post-treatments (i.e., additives and annealing) such that it permits facile morphological modulation. However, the highly planar and crystalline P3T4-VCN exhibits a strong tolerance toward processing treatments. After morphology optimization, the fullerene-based bulk-heterojunction solar cell of tilted P3T4-INCN exhibits a power conversion efficiency (PCE) of 5.68%, which is significantly superior to that of P3T4-VCN:PC71BM (PCE = 1.29%). Our results demonstrate the importance of the terminal end-group for the design of A-D-A-type SMs and their sensitivity toward the postprocessing treatments in optimizing their performance.",

keywords = "A-D-A structure, Coulombic interaction, molecular planarity, organic solar cell, post-treatment",

author = "Kim, {Sang Woo} and Lee, {Yu Jeong} and Lee, {Young Woong} and Koh, {Chang Woo} and Yeran Lee and Kim, {Min Je} and Kin Liao and Cho, {Jeong Ho} and Kim, {Bumjoon J.} and Woo, {Han Young}",

note = "Funding Information: This work was supported by the National Research Foundation (NRF) of Korea (Grants NRF-2016M1A2A2940911, 2017K2A9A2A12000315, 2015M1A2A2057506, and 2015R1D1A1A09056905). We acknowledge additional support for this work from the Research Projects of the KAIST-KUSTAR. Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = nov,

day = "21",

doi = "10.1021/acsami.8b13928",

language = "English",

volume = "10",

pages = "39952--39961",

journal = "ACS Applied Materials and Interfaces",

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T1 - Impact of Terminal End-Group of Acceptor-Donor-Acceptor-type Small Molecules on Molecular Packing and Photovoltaic Properties

AU - Kim, Sang Woo

AU - Lee, Yu Jeong

AU - Lee, Young Woong

AU - Koh, Chang Woo

AU - Lee, Yeran

AU - Kim, Min Je

AU - Liao, Kin

AU - Cho, Jeong Ho

AU - Kim, Bumjoon J.

AU - Woo, Han Young

N1 - Funding Information: This work was supported by the National Research Foundation (NRF) of Korea (Grants NRF-2016M1A2A2940911, 2017K2A9A2A12000315, 2015M1A2A2057506, and 2015R1D1A1A09056905). We acknowledge additional support for this work from the Research Projects of the KAIST-KUSTAR. Publisher Copyright: Copyright © 2018 American Chemical Society.

PY - 2018/11/21

Y1 - 2018/11/21

N2 - In this study, we synthesized two acceptor-donor-acceptor (A-D-A)-type small molecules (SMs) (P3T4-VCN and P3T4-INCN) with different terminal end-groups (dicyanovinyl (VCN) and 2-methylene-3-(1,1-dicyanomethylene)indanone (INCN)) based on the 1,4-bis(thiophenylphenylthiophene)-2,5-difluorophenylene (P3T4) core that possesses high coplanarity because of intrachain noncovalent Coulombic interactions. We investigated the influence of terminal end-groups on intermolecular packing and the resulting electrical and photovoltaic characteristics. A small change in the end-group structure of the SMs induces a significant variation in the torsional structures, molecular packing, and pristine/blend film morphology. It is noteworthy that the less crystalline P3T4-INCN with tilted conformation is highly sensitive to post-treatments (i.e., additives and annealing) such that it permits facile morphological modulation. However, the highly planar and crystalline P3T4-VCN exhibits a strong tolerance toward processing treatments. After morphology optimization, the fullerene-based bulk-heterojunction solar cell of tilted P3T4-INCN exhibits a power conversion efficiency (PCE) of 5.68%, which is significantly superior to that of P3T4-VCN:PC71BM (PCE = 1.29%). Our results demonstrate the importance of the terminal end-group for the design of A-D-A-type SMs and their sensitivity toward the postprocessing treatments in optimizing their performance.

AB - In this study, we synthesized two acceptor-donor-acceptor (A-D-A)-type small molecules (SMs) (P3T4-VCN and P3T4-INCN) with different terminal end-groups (dicyanovinyl (VCN) and 2-methylene-3-(1,1-dicyanomethylene)indanone (INCN)) based on the 1,4-bis(thiophenylphenylthiophene)-2,5-difluorophenylene (P3T4) core that possesses high coplanarity because of intrachain noncovalent Coulombic interactions. We investigated the influence of terminal end-groups on intermolecular packing and the resulting electrical and photovoltaic characteristics. A small change in the end-group structure of the SMs induces a significant variation in the torsional structures, molecular packing, and pristine/blend film morphology. It is noteworthy that the less crystalline P3T4-INCN with tilted conformation is highly sensitive to post-treatments (i.e., additives and annealing) such that it permits facile morphological modulation. However, the highly planar and crystalline P3T4-VCN exhibits a strong tolerance toward processing treatments. After morphology optimization, the fullerene-based bulk-heterojunction solar cell of tilted P3T4-INCN exhibits a power conversion efficiency (PCE) of 5.68%, which is significantly superior to that of P3T4-VCN:PC71BM (PCE = 1.29%). Our results demonstrate the importance of the terminal end-group for the design of A-D-A-type SMs and their sensitivity toward the postprocessing treatments in optimizing their performance.

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KW - Coulombic interaction

KW - molecular planarity

KW - organic solar cell

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SN - 1944-8244

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JO - ACS Applied Materials and Interfaces

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ER -

Impact of Terminal End-Group of Acceptor-Donor-Acceptor-type Small Molecules on Molecular Packing and Photovoltaic Properties

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

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