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

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

6 Scopus Citations
View graph of relations

Author(s)

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

Detail(s)

Original languageEnglish
Pages (from-to)11865-11875
Number of pages11
Journal / PublicationACS Applied Materials and Interfaces
Volume12
Issue number10
Online published2 Mar 2020
Publication statusPublished - 11 Mar 2020
Externally publishedYes

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. © 2020 American Chemical Society.

Research Area(s)

  • benzochalcogenodiazole, bulk heterojunction, organic resistive memory, organic solar cells, spirothienoquinoline

Bibliographic 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.

Citation Format(s)

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 ReviewsRGC 21 - Publication in refereed journalpeer-review