Synthesis of 3,4-Biaryl-2,5-Dichlorothiophene through Suzuki Cross-Coupling and Theoretical Exploration of Their Potential Applications as Nonlinear Optical Materials
Nasir Mahmood,
Nasir Rasool,
Hafiz Mansoor Ikram,
Muhammad Ali Hashmi,
Tariq Mahmood,
Muhammad Zubair,
Gulraiz Ahmad,
Komal Rizwan,
Tahir Rashid,
Umer Rashid
Affiliations
Nasir Mahmood
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Nasir Rasool
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Hafiz Mansoor Ikram
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Muhammad Ali Hashmi
School of Chemical and Physical Sciences, Victoria University of Wellington, Wellington 6012, New Zealand
Tariq Mahmood
Department of Chemistry, COMSATS University, Abbottabad Campus, University Road, Tobe Camp, Abbottabad 22060, Pakistan
Muhammad Zubair
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Gulraiz Ahmad
Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan
Komal Rizwan
Department of Chemistry, Government College Women University, Faisalabad 38000, Pakistan
Tahir Rashid
State Key Laboratory of Metal Matrix Composites, The School of Chemistry & Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China
Umer Rashid
Institute of Advanced Technology, Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
We report herein the efficient one-pot synthesis of 3,4-biaryl-2,5-dichlorothiophene derivatives (2a–2i) 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.
