文献类型：期刊文献

英文题名：Molecular Engineering of Rylene Diimides via Sila-Annulation Toward High-Mobility Organic Semiconductors

作者：Xue, Ning[1];Chen, Kai[2,3];Liu, Guogang[2,3];Wang, Zhaohui[1];Jiang, Wei[1]

机构：[1]Tsinghua Univ, Dept Chem, Key Lab Organ Optoelect & Mol Engn, Beijing 100084, Peoples R China;[2]East China Univ Sci & Technol, Inst Fine Chem, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Key Lab Adv Mat,Feringa Nobel, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Inst Fine Chem, Frontiers Sci Ctr Materiobiol & Dynam Chem, Sch Chem & Mol Engn,Joint Int Res Lab Precis Chem, Shanghai 200237, Peoples R China

年份：2024

卷号：20

期号：17

外文期刊名：SMALL

收录：;EI(收录号：20235015195626);WOS:【SCI-EXPANDED(收录号:WOS:001118517200001)】；

基金：The authors acknowledge Dr. Zhen-Yi Zhang from Bruker (Beijing) Scientific Technology Co., Ltd and Dr. Bin Zhu from State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, Engineering Re-search Centre of Pharmaceutical Process Chemistry, Ministry of Education, Laboratory of Pharmaceutical Crystal Engineering & Technology, East China University of Science and Technology for single-crystal X-ray data collection and refinement. This work was financially supported by the National Natural Science Foundation of China (NSFC) (Nos. 22235005 and 22122503), the National Postdoctoral Program for Innovative Talents (grant no. BX20200128), Shanghai Municipal Science and Technology Major Project grant no. 2018SHZDZX03), and the Shandong Provincial Natural Science Foundation (ZR2019ZD50).

语种：英文

外文关键词：ambipolar transport; organic semiconductors; rylene diimides; sila-annulation; transistors

摘要：The continuous innovation of captivating new organic semiconducting materials remains pivotal in the development of high-performance organic electronic devices. Herein, a molecular engineering by combining sila-annulation with the vertical extension of rylene diimides (RDIs) toward high-mobility organic semiconductors is presented. The unilateral and bilateral sila-annulated quaterrylene diimides (Si-QDI and 2Si-QDI) are designed and synthesized. In particular, the symmetrical bilateral 2Si-QDI exhibits a compact, 1D slipped pi-pi stacking arrangement through the synergistic combination of a sizable pi-conjugated core and intercalating alkyl chains. Combining the appreciable elevated HOMO levels and reduced energy gaps, the single-crystalline organic field-effect transistors (SC-OFETs) based on 2Si-QDI demonstrate exceptional ambipolar transport characteristics with an impressive hole mobility of 3.0 cm2 V-1 s-1 and an electron mobility of 0.03 cm2 V-1 s-1, representing the best ampibolar SC-OFETs based on RDIs. Detailed theoretical calculations rationalize that the larger transfer integral along the pi-pi stacking direction is responsible for the achievement of the superior charge transport. This study showcases the remarkable potential of sila-annulation in optimizing carrier transport performances of polycyclic aromatic hydrocarbons (PAHs). A molecular engineering toward high-mobility organic semiconductors by combining sila-annulation with the vertical extension of rylene diimides is presented. The resultant 2Si-QDI exhibits tunable energy levels and packing arrangement. The single-crystalline organic field-effect transistors demonstrate exceptional ambipolar transport characteristics with an impressive hole mobility of 3.0 cm2 V-1 s-1 and an electron mobility of 0.03 cm2 V-1 s-1.image