| Summary: | We report herein the efficient one-pot synthesis of 3,4-biaryl-2,5-dichlorothiophene derivatives (<b>2a</b>–<b>2i</b>) via a palladium-catalyzed Suzuki cross-coupling reaction. A series of thiophene derivatives were synthesized, starting from 3,4-dibromo-2,5-dichlorothiophene (<b>1</b>) and various arylboronic acids using Pd(PPh<sub>3</sub>)<sub>4</sub> and K<sub>3</sub>PO<sub>4</sub> with moderate to good yields. For further insights about the structure and property relationship, density functional theory (DFT) calculations were performed. A relaxed potential energy surface (PES) scan was performed to locate the minimum energy structure. A frontier molecular orbitals analysis was performed to explain the reactivity of all synthesized derivatives. As the synthesized derivatives had extended conjugations, therefore the first hyperpolarizability (<i>β<sub>o</sub></i>) was calculated to investigate their potential as non-linear optical (NLO) materials and significant <i>β<sub>o</sub></i> values were found for the <b>2b</b> and <b>2g</b> derivatives.
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