CC BY-NC-ND 4.0 · Organic Materials 2020; 02(02): 165-172
DOI: 10.1055/s-0040-1710550
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

Rhodanine-Bridged Core-Expanded Naphthalene Diimide Derivatives for n-Type Semiconductors

a  Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (China)
,
a  Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (China)
,
a  Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (China)
,
a  Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032 (China)
› Author Affiliations
Funding Information The authors would like to thank the National Natural Science Foundation of China (21502218 and 21522209) and the Science and Technology Commission of Shanghai Municipality (19XD1424700 and 18JC1410600) for the financial support.
Further Information

Publication History

Received: 28 February 2020

Accepted after revision: 06 April 2020

Publication Date:
27 May 2020 (online)


Abstract

The core expansion of naphthalene diimides (NDIs) is an effective strategy to modulate frontier molecular orbital energy levels and improve device performances. Herein two new rhodanine-bridged and core-extended NDIs T1 and T2 were designed and synthesized. The rhodanine moiety could act not only as a π-spacer to enlarge the molecular conjugated system, but also as an electron-donating unit to tune the molecular energy levels. As a result, both T1 and T2 showed slightly lower lying LUMO energy levels (< − 4.2 eV) by ca. 0.1 eV and narrower optical band gaps (ca. 1.5 eV) by 0.5 eV compared to those of n-type organic semiconductor (OSC) NDI2DT-DTYM2.The solution-processed organic thin-film transistors based on T1 and T2 exhibited electron motilities in the range of 10−4–10−3 cm2 V−1 s−1, and the inverted perovskite solar cells constructed using T2 as electron transport materials provided a power conversion efficiency value of 8.82%. The results demonstrated that embedding rhodanine units in a NDI2DT-DTYM2 backbone is an effective approach to tune the energy levels and optical properties of OSCs, providing a new way to construct novel n-type OSCs with multifunctional optoelectronic applications.

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1710550.


Supporting Information

 
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