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Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors.

ABSTRACT: A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2-4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their high-lying highest occupied molecular orbital (HOMO) energy levels (EHOMOs), small reorganization energies for hole transport (λholes), and large contribution of sulfur atoms to HOMOs, all of which are desirable for p-type organic semiconductors. Thus, we synthesized nTDs from the corresponding aromatic oligothiophene precursors and then evaluated their physicochemical properties and structural properties. These experimental evaluations of nTDs nicely proved the theoretical predictions, and the largest 4TDs in the series (4,4'''-dihexyl- and 3',4,4″,4'''-tetrahexyl-5H,5'''H-[2,2':5',2″:5″,2'''-quaterthiophene]-5,5'''-dione) can afford solution-processed OFETs showing unipolar p-type behaviors and hole mobility as high as 0.026 cm2 V-1 s-1.

SUBMITTER: Asoh T

PROVIDER: S-EPMC7372439 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors.

Asoh Takato T Kawabata Kohsuke K Takimiya Kazuo K

Materials (Basel, Switzerland) 20200706 13

A series of quinoidal oligothiophenes terminated with carbonyl groups (nTDs, n = 2-4) are studied as p-type organic semiconductors for the active materials in organic field-effect transistors (OFETs) both by the theoretical and experimental approaches. The theoretical calculations clearly show their high-lying highest occupied molecular orbital (HOMO) energy levels (EHOMOs), small reorganization energies for hole transport (λholes), and large con ...[more]

PMID: 32640695

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Project description:In the present investigation, quantum chemical calculations have been performed in a systematic way to explore the optoelectronic, charge transfer, and nonlinear optical (NLO) properties of different bis(dicyanomethylene) end-functionalized quinoidal oligothiophenes. The effect of different conformations (linking modes of thiophene rings) on conformational, optoelectronic, and NLO properties are studied from the best-performed dimer to octamer. The optical and NLO properties of all the selected systems (1-7) are calculated by means of density functional theory (DFT) methods. Among all the designed compounds, the largest linear isotropic (αiso) polarizability value of 603.1 × 10-24 esu is shown by compound 7 which is ∼12, ∼16, ∼9, ∼11, ∼10, and ∼4 times larger as compared to compounds 1-6, respectively. A relative investigation is performed considering the expansion in third-order NLO polarizability as a function of size and conformational modes. Among all the investigated systems, system 7 shows the highest value of static second hyperpolarizability ⟨γ⟩ with an amplitude of 7607 × 10-36 esu at the M06/6-311G** level of theory, which is ∼521, ∼505, ∼38, ∼884, ∼185, and ∼15 times more than that of compounds 1-6, respectively. The extensively larger ⟨γ⟩ amplitude of compound 7 with higher oscillator strength and lower transition energy indicates that NLO properties are remarkably dependent upon linking modes of thiophene rings and its chain length. Furthermore, to trace the origin of higher nonlinearities, TD-DFT calculations are also performed at the same TD-M06/6-311G** level of theory. Additionally, a comprehensive understanding of the effect of structure/property relationship on the NLO polarizabilities of these investigated quinoidal oligothiophenes is obtained through the inspection of Frontier molecular orbitals, the density of states (TDOS and PDOS), and molecular electrostatic potential diagrams including the transition density matrix. Hence, the current examination will not just feature the NLO capability of entitled compounds yet additionally incite the interest of experimentalists to adequately modify the structure of these oligothiophenes for efficient optical and NLO applications.

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Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors.

Publications

Carbonyl-Terminated Quinoidal Oligothiophenes as p-Type Organic Semiconductors.

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