Theoretical study of charge-transport and optical properties of organic crystals: 4,5,9,10-pyrenediimides

Abstract

This work presents a systematic study of the conducting and optical properties of a family of aromatic diimides reported recently and discusses the influences of side-chain substitution on the reorganization energies, crystal packing, electronic couplings and charge injection barrier of 4,5,9,10-pyrenediimide (PyDI). Quantum-chemical calculations combined with the Marcus–Hush electron transfer theory revealed that the introduction of a side chain into 4,5,9,10-pyrenediimide increases intermolecular steric interactions and hinders close intermolecular π–π stacking, which results in weak electronic couplings and finally causes lower intrinsic hole and electron mobility in t-C5-PyDI (μh = 0.004 cm2 V−1 s−1 and μe = 0.00003 cm2 V−1 s−1) than in the C5-PyDI crystal (μh = 0.16 cm2 V−1 s−1 and μe = 0.08 cm2 V−1 s−1). Furthermore, electronic spectra of C5-PyDI were simulated and time-dependent density functional theory calculation results showed that the predicted fluorescence maximum of t-C5-PyDI, corresponding to an S 1→S 0 transition process, is located at 485 nm, which is close to the experimental value (480 nm).

Powder X-ray diffraction as a powerful tool to exploit in organic electronics: shedding light on the first N,N′,N′′-trialkyldiindolocarbazole

“…Some of the enticing advantages associated with them are the easy modulation of their properties, their lower cost and the feasibility to fabricate large-area, lightweight and flexible displays (Bronstein et al, 2020;Yao et al, 2016). In fact, their applicability in devices such as organic thin-film transistors (OTFTs) and organic light-emitting diodes (OLEDs) have been extensively demonstrated (Wang et al, 2017;Huang et al, 2019). Nevertheless, the demand for improved materials, especially in terms of charge transport and air stability, dictates further investigation.…”

Quantitative Prediction of Anisotropic Carrier Mobilities for BN-Embedded Perylene Diimides in Three-Dimensional Space

“…The HOMO and LUMO distributions are perpendicular to the 6-CH molecular plane, which shows obvious π bonding orbital character and π* antibonding orbital character, respectively. Similar with other polycyclic aromatic compounds, such as 4,5,9,10-pyrenediimide, the HOMO of 6-CH was mainly located on the O atoms and CC bonds that aligned predominantly along the short molecular axis, while the LUMOs were mainly located on the O atoms and CC bonds that aligned predominantly along the long axis. These different distribution characters of HOMO and LUMO result in the remarkable difference in the V h and V e .…”

5‐Bromosalicylaldehyde: Theoretical, Experimental and Spectroscopic (FT‐IR, Raman, H1 and C13‐NMR, UV‐Vis) Studies and Their Photovoltaic Parameters

“…[30] The lower reorganization energy supports faster electron transit. The calculation of hole reorganization energy (λ h ) and electron reorganization energy (λ e ) may be performed using Equations ( 4) and ( 5), [31] respectively. Furthermore, λ total is defined as the sum of reorganization energy of the hole and those of the electron.…”