A series of novel imide-functionalized ladder-type heteroarenes with well-defined structure and controllable conjugation lengths were synthesized and characterized. The synthetic route shows remarkable efficacy for constructing the electron-deficient ladder backbones. π-Conjugation extension leads to narrowed band gaps with enhanced electron affinities. The ladder arenes are incorporated into organic thin-film transistors, and show encouraging electron mobilities of 0.013-0.045 cm V s . The heteroarenes reported here provide a remarkable platform for fundamental physicochemical studies and materials innovation in organic electronics.
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http://dx.doi.org/10.1002/anie.201702225 | DOI Listing |
Org Lett
November 2024
College of Chemistry and Materials Science, Hebei University, Baoding, 071002, PR China.
Fluorenylidene-xanthene and related polycyclic systems are typical examples of bistricyclic aromatic enes (BAEs); however, polycyclic systems of fluorenylidene-xanthene are relatively scarce. Here we synthesized a series of novel ladder-type polycyclic systems containing fluorenylidene-xanthene units, differing from the classic Barton's two-fold extrusion reaction. In the new synthetic scheme, the very popular Suzuki reaction was first used to couple the corresponding precursors, then a catalyst-free nucleophilic aromatic substitution reaction between Ar-F and Ar-OH groups in the backbone afforded ladder-type -heteroarenes.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
November 2024
State Key Laboratory of Applied Organic Chemistry (SKLAOC), Key Laboratory of Special Function Materials and Structure Design (MOE), College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
Small
October 2023
Department of Chemical Engineering, National Tsing Hua University, Hsinchu, 300044, Taiwan.
Conjugated polymers (CPs) have recently gained increasing attention as photocatalysts for sunlight-driven hydrogen evolution. However, they suffer from insufficient electron output sites and poor solubility in organic solvents, severely limiting their photocatalytic performance and applicability. Herein, solution-processable all-acceptor (A -A )-type CPs based on sulfide-oxidized ladder-type heteroarene are synthesized.
View Article and Find Full Text PDFACS Appl Mater Interfaces
February 2023
Department of Materials Science and Engineering, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen 518055, Guangdong, China.
Chem Asian J
September 2018
Department of Materials Science and Engineering and The Shenzhen Key Laboratory for Printed Organic Electronics, Southern University of Science and Technology (SUSTech), No. 1088, Xueyuan Road, Shenzhen, Guangdong, 518055, China.
The fusion of heteroaromatic rings into ladder-type heteroarenes can stabilize frontier molecular orbitals and lead to improved physicochemical properties that are beneficial for applications in various optoelectronic devices. Thus, ladder-type heteroarenes, which feature highly planar backbones and well-delocalized π conjugation, have recently emerged as a promising type of organic semiconductor with excellent device performance in organic photovoltaics (OPVs) and organic field-effect transistors (OFETs). In this Focus Review, we summarize the recent advances in ladder-type heteroarene-based organic semiconductors, such as hole- and electron-transporting molecular semiconductors, and fully ladder-type conjugated polymers towards their applications in OPVs and OFETs.
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