Tuning the donor–acceptor interactions in phase-segregated block molecules

Abstract

The assembly of donor–acceptor molecules via charge transfer (CT) interactions gives rise to highly ordered nanomaterials with appealing electronic properties. Here, we present the synthesis and bulk co-assembly of pyrene (Pyr) and naphthalenediimide (NDI) functionalized oligodimethylsiloxanes (oDMS) of discrete length. We tune the donor–acceptor interactions by connecting the pyrene and NDI to the same oligomer, forming a heterotelechelic block molecule (NDI-oDMSPyr), and to two separate oligomers, giving Pyr and NDI homotelechelic block molecules (Pyr-oDMS and NDI-oDMS). Liquid crystalline materials are obtained for binary mixtures of Pyr-oDMS and NDI-oDMS, while crystallization of the CT dimers occurred for the heterotelechelic NDI-oDMS-Pyr block molecule. The synergy between crystallization and phase-segregation coupled with the discrete length of the oDMS units allows for perfect order and sharp interfaces between the insulating siloxane and CT layers composed of crystalline CT dimers. We were able to tune the lamellar domain spacing and donor–acceptor CT interactions by applying pressures up to 6 GPa on the material, making the system promising for soft-material nanotechnologies. These results demonstrate the importance of the molecular design to tune the CT interactions and stability of a CT material.

Graphical abstract: Tuning the donor–acceptor interactions in phase-segregated block molecules

Supplementary files

Article information

Article type
Communication
Submitted
17 Jul 2021
Accepted
17 Sep 2021
First published
20 Sep 2021
This article is Open Access
Creative Commons BY license

Mater. Horiz., 2021, Advance Article

Tuning the donor–acceptor interactions in phase-segregated block molecules

B. A. G. Lamers, M. H. C. van Son, F. V. de Graaf, B. W. L. van den Bersselaar, B. F. M. de Waal, K. Komatsu, H. Sato, T. Aida, J. A. Berrocal, A. R. A. Palmans, G. Vantomme, S. C. J. Meskers and E. W. Meijer, Mater. Horiz., 2021, Advance Article , DOI: 10.1039/D1MH01141C

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