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.

Computational Design of Crescent Shaped Promising Nonfullerene Acceptors with 1,4-Dihydro-2,3-quinoxalinedione Core and Different Electron-withdrawing Terminal Units for Photovoltaic Applications

“…41 All possible crystal structures are selected by energy minimization of crystals with the most common space groups such as P2 1 ∕C, P1, P1, Pbca, P2 1 2 1 2 1 , P2 1 , C2∕c, Pna2 1 , Cc, Pbcn, and C2. 4,42,43,44,45 Crystal structure prediction method within the Polymorph Predictor module relies on Monte Carlo simulation which is a stochastic process. To assess the completeness of the search within this module, we have repeated the simulations for several times for each initial molecular structure until the same low energy crystal structures are produced.…”

“…We generated large number of possible polymorphs using Dreiding force field parametrization which is considered to be a reasonable choice for organic molecules. 4,43,44,45 The charge transfer integrals of the designed NFAs are evaluated using the site energy correction method at the PW91/TZP level of theory using the ADF program. 46,47 The PW91/TZP theoretical level has been widely used to evaluate charge transfer integrals of organic molecules.…”

“…Crystal structures of the designed NFAs have been predicted employing the most reliable Dreiding force field within the Polymorph Predictor module of the BIOVIA Materials Studio17 based on their optimized gas-phase conformations . All possible crystal structures are selected by energy minimization of crystals with the most common space groups such as P 2 1 / C , P 1, P 1̅, Pbca , P 2 1 2 1 2 1 , P 2 1 , C 2/ c , Pna 2 1 , Cc , Pbcn , and C 2. ,− The crystal structure prediction method within the Polymorph Predictor module relies on Monte Carlo simulation which is a stochastic process. To assess the completeness of the search within this module, we have repeated the simulations for several times for each initial molecular structure until the same low energy crystal structures are produced.…”

“…To assess the completeness of the search within this module, we have repeated the simulations for several times for each initial molecular structure until the same low energy crystal structures are produced. We generated a large number of possible polymorphs using Dreiding force field parametrization which is considered to be a reasonable choice for organic molecules. ,− The charge transfer integrals of the designed NFAs are evaluated using the site energy correction method at the PW91/TZP level of theory using the ADF program. , The PW91/TZP theoretical level was widely used to evaluate charge transfer integrals of organic molecules. − Further, to model the interface between the PM6 donor and the NFAs, we performed end-to-end acceptor–acceptor (A-A) stacking. In the A-A stacking, the stacking occurs between the electron-withdrawing end groups of the NFAs and the electron withdrawing unit (A) of the polymer PM6 donor.…”

Computational study of electron transport in halogen incorporated diindenotetracene compounds: crystal structure, charge transport and optoelectronic properties

“…7,8 The development of air-stable n-type OSCs characterized by low lying LUMO energies (oÀ3.9 eV) and high electron affinity (EA) values (43.0 eV) has been a major challenge in the field of organic electronics. [9][10][11][12][13][14] To meet this challenge, several experimental and theoretical studies have been carried out by many authors to develop highperformance n-type and air-stable OSCs. [15][16][17] One of the promising means that has been mostly highlighted to enhance the n-type characteristics in organic materials is the incorporation of electron-withdrawing groups such as -F, -Cl, -Br, and -CN at the peripheral and bay positions of p-conjugated systems.…”