Issue 2, 2022

Molecular tetrominoes: selective masking of the donor π-face to control the configuration of donor–acceptor complexes

Abstract

Understanding the doping mechanism in organic semiconductors and generating molecular design rules to control the doping process are crucial for improving the performance of organic electronics. Even though controlling the location and orientation of the dopant along the semiconductor backbone is an important step in the doping mechanism, studies in this direction are scarce as it is a challenging task. To address this, herein, we incorporated π-face masked (strapped) units in 1,4-bis(phenylethynylene)benzene (donor) to control the acceptor (dopant) location along the trimer, donor–acceptor binding strength, and acceptor ionization. Two strapped trimers, PCP and CPC, are synthesized with control over the location of the strapped repeat unit in the trimer. The trimers are complexed with the 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) acceptor in solution. DFT calculations show that DDQ residing on the non-strapped repeat unit (the percentage of this configuration is at least ca. 73%) has the highest binding energy for both PCP and CPC. The percentage of dopant ionization is higher in the case of strapped trimers (PCP and CPC) compared to that of linear control trimers (PLP and LPL) and the completely non-strapped (PPP) trimer. The percentage of dopant ionization increased by 15 and 59% in the case of PCP and CPC respectively compared to that of PPP.

Graphical abstract: Molecular tetrominoes: selective masking of the donor π-face to control the configuration of donor–acceptor complexes

Supplementary files

Article information

Article type
Paper
Submitted
23 Nov 2021
Accepted
25 Nov 2021
First published
02 Dec 2021

Org. Biomol. Chem., 2022,20, 375-386

Molecular tetrominoes: selective masking of the donor π-face to control the configuration of donor–acceptor complexes

J. L. Sartucci, A. Maity, M. Mohanan, J. Bertke, M. Kertesz and N. Gavvalapalli, Org. Biomol. Chem., 2022, 20, 375 DOI: 10.1039/D1OB02293H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements