π-Conjugated Molecules Containing Naphtho[2,3-b]thiophene and Their Derivatives: Theoretical Design for Organic Semiconductors

Abstract

We performed a theoretical investigation on a series of π-conjugated organic molecules containing naphtho[2,3-b]thiophene and their derivatives using density functional theory calculations. All molecules considered exhibit planar structures and aromaticity. Energy levels of frontier orbitals and reduction and oxidation potentials of these compounds predicted by our solvation model reveal good agreement with available experimental values. The UV absorption spectra point out a clear trend that maximum peaks corresponding HOMO–LUMO transitions are red-shifted: (i) from compounds containing O to those containing Se, (ii) from dimers 1a–3a and 1b–3b to trimers 4a–6a and 4b–6b, and (iii) from parent compounds 1a–6a to perfluorinated derivatives 1b–6b. Parent compounds 1a–6a can be considered as p-type semiconducting materials with low reorganization energies, high transfer integrals, and hole mobility. Perfluorinated compounds 1b–6b are suggested to be very good candidates for ambipolar semiconducting materials. Introduction of fused-ring core molecules considerably improves the charge transport characteristics of the co-oligomers 4a–6a and 4b–6b as compared to those of corresponding molecules 1a–3a and 1b–3b. Accordingly, the former have lower reorganization energies, higher electron transfer integrals, and higher rates of charge hopping.

Computational Designing of Low Energy Gap Small Molecule Acceptors for Organic Solar Cells

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Quantum Mechanical-Based Quantitative Structure–Property Relationships for Electronic Properties of Two Large Classes of Organic Semiconductor Materials: Polycyclic Aromatic Hydrocarbons and Thienoacenes

“…They are used in production of organic light-emitting diodes (OLEDs), organic field-effect transistors, organic thin-film transistors, and organic photovoltaics. 1−16…”

Effects of Mechanical Deformation on the Opto-Electronic Responses, Reactivity, and Performance of Conjugated Polymers: A DFT Study

“…PANI is used in electro-rheological fluids, sensors, supercapacitors and rechargeable batteries [ 46 , 47 , 48 , 49 , 50 ]. PT is widely used in polymer-based OLEDs (PLEDs), OSCs, and chemical sensors due to its conductive, luminescence, and electrochromic properties, as well as its high versatility of synthesis [ 51 , 52 , 53 ]. PPV derivatives are also commonly used in PLEDs and OSCs [ 54 , 55 , 56 ].…”