Affiliation:
1. College of Chemical and Material Engineering, Quzhou University, Quzhou 324000, China
2. Shenzhen Research Institute of Nankai University, Nankai University, Shenzhen 518083, China
3. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
Abstract
The construction of high-performance n-type semiconductors is crucial for the advancement of organic electronics. As an attractive n-type semiconductor, molecular systems based on perylene diimide derivatives (PDIs) have been extensively investigated over recent years. Owing to the fascinating aggregated structure and high performance, S-heterocyclic annulated PDIs (SPDIs) are receiving increasing attention. However, the relationship between the structure and the electrical properties of SPDIs has not been deeply revealed, restricting the progress of PDI-based organic electronics. Here, we developed two novel SPDIs with linear and dendronized substituents in the imide position, named linear SPDI and dendronized SPDI, respectively. A series of structural and property characterizations indicated that linear SPDI formed a long-range-ordered crystalline structure based on helical supramolecular columns, while dendronized SPDI, with longer alkyl side chains, formed a 3D-ordered crystalline structure at a low temperature, which transformed into a hexagonal columnar liquid crystal structure at a high temperature. Moreover, no significant charge carrier transport signal was examined for linear SPDI, while dendronized SPDI had a charge carrier mobility of 3.5 × 10−3 cm2 V−1 s−1 and 2.1 × 10−3 cm2 V−1 s−1 in the crystalline and liquid crystalline state, respectively. These findings highlight the importance of the structure–function relationship in PDIs, and also offer useful roadmaps for the design of high-performance organic electronics for down-to-earth applications.
Funder
Zhejiang Provincial Natural Science Foundation
Quzhou Science and Technology Bureau Projects
Quzhou 115 Talent Project