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Symmetry 2018, 10(12), 766; https://doi.org/10.3390/sym10120766

Synthesis of 3,4-Biaryl-2,5-Dichlorothiophene through Suzuki Cross-Coupling and Theoretical Exploration of Their Potential Applications as Nonlinear Optical Materials

1
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
2
School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
3
Department of Chemistry, University of Management and Technology, C-II, Johar Town, Lahore 54770, Pakistan
4
Department of Chemistry, COMSATS University, Abbottabad Campus, University Road, Tobe Camp, Abbottabad 22060, Pakistan
5
Department of Chemistry, Government College Women University, Faisalabad 38000, Pakistan
6
State Key Laboratory of Metal Matrix Composites, The School of Chemistry & Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
7
Institute of Advanced Technology, Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
*
Authors to whom correspondence should be addressed.
Received: 22 September 2018 / Revised: 18 October 2018 / Accepted: 23 October 2018 / Published: 18 December 2018
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Abstract

We report herein the efficient one-pot synthesis of 3,4-biaryl-2,5-dichlorothiophene derivatives (2a2i) via a palladium-catalyzed Suzuki cross-coupling reaction. A series of thiophene derivatives were synthesized, starting from 3,4-dibromo-2,5-dichlorothiophene (1) and various arylboronic acids using Pd(PPh3)4 and K3PO4 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 (βo) was calculated to investigate their potential as non-linear optical (NLO) materials and significant βo values were found for the 2b and 2g derivatives. View Full-Text
Keywords: Suzuki cross-coupling reaction; thiophene; Pd (PPh3)4; NLO; PES; density functional theory Suzuki cross-coupling reaction; thiophene; Pd (PPh3)4; NLO; PES; density functional theory
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Mahmood, N.; Rasool, N.; Ikram, H.M.; Hashmi, M.A.; Mahmood, T.; Zubair, M.; Ahmad, G.; Rizwan, K.; Rashid, T.; Rashid, U. Synthesis of 3,4-Biaryl-2,5-Dichlorothiophene through Suzuki Cross-Coupling and Theoretical Exploration of Their Potential Applications as Nonlinear Optical Materials. Symmetry 2018, 10, 766.

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