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Issue 18, 2020
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Surface-induced enantiomorphic crystallization of achiral fullerene derivatives in thin films

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Abstract

The chirality of organic semiconductors is important for various applications in optoelectronics and spintronics. Here, we propose a new strategy to induce structural chirality in achiral organic semiconductors in thin films. Enantiomeric fullerene derivatives (S)-pSi and (R)-pSi, which have oligo(dimethylsiloxane) as a low-surface-energy moiety, were synthesized and used as surface-segregated monolayers (SSMs) in spin-coated films of several achiral fullerene derivatives. Upon thermal annealing, the presence of the chiral SSMs led to the crystallization of the fullerenes in the films as an SSM-induced crystal phase at lower temperatures. The crystallized films showed circular dichroism ascribed to the fullerene absorption, the sign and the intensity of which depended on the handedness of the SSM molecules and the film thickness, respectively. These results indicate that the achiral fullerene derivatives in the films were induced by the SSMs to crystallize into enantiomorphic crystals. Our approach to inducing chirality in organic thin films is compatible with many device applications.

Graphical abstract: Surface-induced enantiomorphic crystallization of achiral fullerene derivatives in thin films

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Supplementary files

Article information


Submitted
27 Feb 2020
Accepted
17 Apr 2020
First published
17 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 4702-4708
Article type
Edge Article

Surface-induced enantiomorphic crystallization of achiral fullerene derivatives in thin films

C. Wang, H. Hao, D. Hashizume and K. Tajima, Chem. Sci., 2020, 11, 4702
DOI: 10.1039/D0SC01163K

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