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Updated: Sep 12, 2026

Ultrahigh Density Array of Vertically Aligned Small-molecular Organic Nanowires on Arbitrary Substrates
Published on: June 18, 2013
Rylene Diimides Featuring Quadruple C─H···(O═C) Locking for High-Mobility Organic Semiconductors
Shunlong Hu1, Zijie Dai2, Xin Jin1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center For Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai, China.
Abstract:
Polycyclic aromatic hydrocarbons with large conjugated planes and low reorganization energy serve as an ideal molecular platform for organic semiconductors; however, precisely controlling their aggregated structures to achieve large transfer integrals and thus excellent charge transport efficiency remains a significant challenge. Herein, we design and synthesize a sila-annulated hexarylene diimide (2Si-HDI) featuring imide units at both peri-positions and two silole rings at the central bay-positions. Through the quadruple C─H···(O═C) locking between carbonyls of the diimide groups and the hydrogen atoms of the 1,1'-diethylsilyl groups at the silole rings, we realized the first 1D slipped π-π stacking of ultra-long rylenes (naphthalene unit ≥ 6), providing groundbreaking guidance for the well-ordered π-π self-assembly of large planar PAHs relevant to armchair graphene nanoribbons. The single-crystalline organic field-effect transistor properties of 2Si-HDI exhibit hole/electron mobilities up to 3.08/0.06 cm2 V-1 s-1. Theoretical calculations reveal hole/electron transfer integrals of 2Si-HDI as high as 110.08/78.08 meV along the π-π stacking direction, rationalizing its superior charge transport performance.
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