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

^*Corresponding author for this work

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

20 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.

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Keywords

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

ASJC Scopus subject areas

General Materials Science

Access to Document

10.1021/acsami.8b13928

Cite this

@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",

issn = "1944-8244",

publisher = "American Chemical Society",

number = "46",

}

TY - JOUR

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.

KW - A-D-A structure

KW - Coulombic interaction

KW - molecular planarity

KW - organic solar cell

KW - post-treatment

UR - https://www.scopus.com/pages/publications/85056845518

U2 - 10.1021/acsami.8b13928

DO - 10.1021/acsami.8b13928

M3 - Article

C2 - 30379525

AN - SCOPUS:85056845518

SN - 1944-8244

VL - 10

SP - 39952

EP - 39961

JO - ACS Applied Materials and Interfaces

JF - ACS Applied Materials and Interfaces

IS - 46

ER -

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

Abstract

Bibliographical note

UN SDGs

Keywords

ASJC Scopus subject areas

Access to Document

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