Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications

Panpan Li; Chin-Yiu Chan; Shiu-Lun Lai; Hing Chan; Ming-Yi Leung; Eugene Yau-Hin Hong; Jingwen Li; Hongbin Wu; Mei-Yee Chan; Vivian Wing-Wah Yam

doi:10.1021/acsami.9b19746

Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications

Panpan Li
, Chin-Yiu Chan
, Shiu-Lun Lai
, Hing Chan
, Ming-Yi Leung
, Eugene Yau-Hin Hong
, Jingwen Li
, Hongbin Wu
, Mei-Yee Chan^*
, Vivian Wing-Wah Yam^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

12 Citations (Scopus)

Abstract

A new electron-rich spirothienoquinoline unit, ^tBuSAF-Th, has been developed via incorporation of a thienyl unit instead of a phenyl unit into the six-membered ring of the spiroacridine (SAF) and utilized for the first time as a building block for constructing small-molecule electron donors in organic solar cells (OSCs) and as active layers in organic resistive memory devices. The resulting three-dimensional spirothienoquinoline-containing 1-4 exhibit high-lying highest occupied molecular orbital (HOMO) energy levels. By the introduction of electron-deficient benzochalcogenodiazole linkers, with the chalcogen atoms being varied from O to S and Se, a progressively lower lowest unoccupied molecular orbital (LUMO) energy level has been achieved while keeping the HOMO energy levels similar. This strategy has allowed an enhanced light-harvesting ability without compromising open-circuit voltage (V_oc) in vacuum-deposited bulk heterojunction OSCs using 1-4 as donors and C₇₀ as the acceptor. Good photovoltaic performances with power conversion efficiencies (PCEs) of up to 3.86% and high short-circuit current densities (J_sc) of up to 10.84 mA cm^-2 have been achieved. In addition, organic resistive memory devices fabricated with these donor-acceptor small molecules exhibit binary logic memory behaviors with long retention times and high on/off current ratios. This work indicates that the spirothienoquinoline moiety is a potential building block for constructing multifunctional organic electronic materials. © 2020 American Chemical Society.

Original language	English
Pages (from-to)	11865-11875
Number of pages	11
Journal	ACS Applied Materials and Interfaces
Volume	12
Issue number	10
Online published	2 Mar 2020
DOIs	https://doi.org/10.1021/acsami.9b19746
Publication status	Published - 11 Mar 2020
Externally published	Yes

Bibliographical note

Funding Information:
V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People’s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project.

Funding Information:
V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People?s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Funding

V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People’s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project.

UN SDGs

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

SDG 7 Affordable and Clean Energy

Research Keywords

benzochalcogenodiazole
bulk heterojunction
organic resistive memory
organic solar cells
spirothienoquinoline

RGC Funding Information

RGC-funded

Access Output

10.1021/acsami.9b19746

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@article{af367044db834e558e35672488daab21,

title = "Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications",

abstract = "A new electron-rich spirothienoquinoline unit, tBuSAF-Th, has been developed via incorporation of a thienyl unit instead of a phenyl unit into the six-membered ring of the spiroacridine (SAF) and utilized for the first time as a building block for constructing small-molecule electron donors in organic solar cells (OSCs) and as active layers in organic resistive memory devices. The resulting three-dimensional spirothienoquinoline-containing 1-4 exhibit high-lying highest occupied molecular orbital (HOMO) energy levels. By the introduction of electron-deficient benzochalcogenodiazole linkers, with the chalcogen atoms being varied from O to S and Se, a progressively lower lowest unoccupied molecular orbital (LUMO) energy level has been achieved while keeping the HOMO energy levels similar. This strategy has allowed an enhanced light-harvesting ability without compromising open-circuit voltage (Voc) in vacuum-deposited bulk heterojunction OSCs using 1-4 as donors and C70 as the acceptor. Good photovoltaic performances with power conversion efficiencies (PCEs) of up to 3.86\% and high short-circuit current densities (Jsc) of up to 10.84 mA cm-2 have been achieved. In addition, organic resistive memory devices fabricated with these donor-acceptor small molecules exhibit binary logic memory behaviors with long retention times and high on/off current ratios. This work indicates that the spirothienoquinoline moiety is a potential building block for constructing multifunctional organic electronic materials. {\textcopyright} 2020 American Chemical Society.",

keywords = "benzochalcogenodiazole, bulk heterojunction, organic resistive memory, organic solar cells, spirothienoquinoline",

author = "Panpan Li and Chin-Yiu Chan and Shiu-Lun Lai and Hing Chan and Ming-Yi Leung and Hong, \{Eugene Yau-Hin\} and Jingwen Li and Hongbin Wu and Mei-Yee Chan and Yam, \{Vivian Wing-Wah\}",

note = "Funding Information: V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People{\textquoteright}s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project. Funding Information: V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People?s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "11",

doi = "10.1021/acsami.9b19746",

language = "English",

volume = "12",

pages = "11865--11875",

journal = "ACS Applied Materials and Interfaces",

issn = "1944-8244",

publisher = "American Chemical Society",

number = "10",

}

Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications. / Li, Panpan; Chan, Chin-Yiu; Lai, Shiu-Lun et al.
In: ACS Applied Materials and Interfaces, Vol. 12, No. 10, 11.03.2020, p. 11865-11875.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications

AU - Li, Panpan

AU - Chan, Chin-Yiu

AU - Lai, Shiu-Lun

AU - Chan, Hing

AU - Leung, Ming-Yi

AU - Hong, Eugene Yau-Hin

AU - Li, Jingwen

AU - Wu, Hongbin

AU - Chan, Mei-Yee

AU - Yam, Vivian Wing-Wah

N1 - Funding Information: V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People’s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project. Funding Information: V.W.-W.Y. acknowledges the support from HKU University Research Committee (URC) Strategically Oriented Research Theme (SORT) on Functional Materials for Molecular Electronics. This work has been fully supported by the General Research Fund (GRF) grant from the Research Grants Council of the Hong Kong Special Administrative Region, People?s Republic of China (HKU 17306219). P.L. acknowledges the receipt of a postgraduate studentship from The University of Hong Kong. The National Facility for Protein Science in Shanghai (NFPS) at Shanghai Synchrotron Radiation Facility is thanked for providing the beam time of the BL17B beamline. Dr. L.-Y. Yao and Mr. L. Yan are acknowledged for their assistance in X-ray crystal data collection and analyses. Dr. Maggie Ng is thanked for her help in the computational studies, and Mr. Wai-Lung Cheung is acknowledged for his help in thin-film deposition for AFM measurements. Dr. Hok-Lai Wong and Dr. Yat-Hin Cheng are gratefully acknowledged for their helpful discussions on the project. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/3/11

Y1 - 2020/3/11

N2 - A new electron-rich spirothienoquinoline unit, tBuSAF-Th, has been developed via incorporation of a thienyl unit instead of a phenyl unit into the six-membered ring of the spiroacridine (SAF) and utilized for the first time as a building block for constructing small-molecule electron donors in organic solar cells (OSCs) and as active layers in organic resistive memory devices. The resulting three-dimensional spirothienoquinoline-containing 1-4 exhibit high-lying highest occupied molecular orbital (HOMO) energy levels. By the introduction of electron-deficient benzochalcogenodiazole linkers, with the chalcogen atoms being varied from O to S and Se, a progressively lower lowest unoccupied molecular orbital (LUMO) energy level has been achieved while keeping the HOMO energy levels similar. This strategy has allowed an enhanced light-harvesting ability without compromising open-circuit voltage (Voc) in vacuum-deposited bulk heterojunction OSCs using 1-4 as donors and C70 as the acceptor. Good photovoltaic performances with power conversion efficiencies (PCEs) of up to 3.86% and high short-circuit current densities (Jsc) of up to 10.84 mA cm-2 have been achieved. In addition, organic resistive memory devices fabricated with these donor-acceptor small molecules exhibit binary logic memory behaviors with long retention times and high on/off current ratios. This work indicates that the spirothienoquinoline moiety is a potential building block for constructing multifunctional organic electronic materials. © 2020 American Chemical Society.

AB - A new electron-rich spirothienoquinoline unit, tBuSAF-Th, has been developed via incorporation of a thienyl unit instead of a phenyl unit into the six-membered ring of the spiroacridine (SAF) and utilized for the first time as a building block for constructing small-molecule electron donors in organic solar cells (OSCs) and as active layers in organic resistive memory devices. The resulting three-dimensional spirothienoquinoline-containing 1-4 exhibit high-lying highest occupied molecular orbital (HOMO) energy levels. By the introduction of electron-deficient benzochalcogenodiazole linkers, with the chalcogen atoms being varied from O to S and Se, a progressively lower lowest unoccupied molecular orbital (LUMO) energy level has been achieved while keeping the HOMO energy levels similar. This strategy has allowed an enhanced light-harvesting ability without compromising open-circuit voltage (Voc) in vacuum-deposited bulk heterojunction OSCs using 1-4 as donors and C70 as the acceptor. Good photovoltaic performances with power conversion efficiencies (PCEs) of up to 3.86% and high short-circuit current densities (Jsc) of up to 10.84 mA cm-2 have been achieved. In addition, organic resistive memory devices fabricated with these donor-acceptor small molecules exhibit binary logic memory behaviors with long retention times and high on/off current ratios. This work indicates that the spirothienoquinoline moiety is a potential building block for constructing multifunctional organic electronic materials. © 2020 American Chemical Society.

KW - benzochalcogenodiazole

KW - bulk heterojunction

KW - organic resistive memory

KW - organic solar cells

KW - spirothienoquinoline

UR - https://www.scopus.com/pages/publications/85081222887

U2 - 10.1021/acsami.9b19746

DO - 10.1021/acsami.9b19746

M3 - RGC 21 - Publication in refereed journal

C2 - 32115950

AN - SCOPUS:85081222887

SN - 1944-8244

VL - 12

SP - 11865

EP - 11875

JO - ACS Applied Materials and Interfaces

JF - ACS Applied Materials and Interfaces

IS - 10

ER -

Three-Dimensional Spirothienoquinoline-Based Small Molecules for Organic Photovoltaic and Organic Resistive Memory Applications

Abstract

Bibliographical note

Funding

UN SDGs

Research Keywords

RGC Funding Information

Access Output

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