Issue 21, 2021

Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

Abstract

In this study, we present an effective molecular design strategy to develop the n-type charge transport characteristics in organic semiconductors, using ring-fused double perylene diimides (DPDIs) as the model compounds. These dimeric-PDIs are formed by joining two separate PDI-units along their bay positions through ring fusion with pyrene, coronene and their N-doped counterparts. The bridging type has a significant steric effect at the annulation positions and controls the molecular geometry, mostly imposing buckling in the structure. The crystal structures of the designed compounds are also theoretically predicted. Thereafter, electronic structure parameters, molecular packing motifs, charge coupling strength and anisotropic mobilities were investigated to understand the charge transport efficiency of these systems. Among all the studied molecules, the 4N-coronene-fused DPDI (DPDI-6) is found to possess a lower LUMO level and a high EA, suggesting air-stable electron injection. Besides, DPDI-6 shows strong intermolecular electron coupling and possesses high electron mobility (μe = 5.31 × 10−2 cm2 V−1 s−1), which is better as compared with the other DPDI-compounds reported here. The DPDIs also possess optical absorption in the UV-visible region, opening up possible applications in organic photovoltaics. Besides, from the non-linear optical (NLO) analysis, DPDI-3 is found to possess the highest first-order hyperpolarizability, which is even better as compared with the reference compound urea, making it a promising candidate for NLO applications.

Graphical abstract: Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

Supplementary files

Article information

Article type
Paper
Submitted
01 Jan 2021
Accepted
22 Apr 2021
First published
21 May 2021

Phys. Chem. Chem. Phys., 2021,23, 12329-12339

Rational design and crystal structure prediction of ring-fused double-PDI compounds as n-channel organic semiconductors: a DFT study

S. Debata, S. R. Sahoo, R. Khatua and S. Sahu, Phys. Chem. Chem. Phys., 2021, 23, 12329 DOI: 10.1039/D1CP00008J

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