Synthesis and X-ray single crystal study of 5-(4,4,5,5 – tetramethyl – 1,3,2 –dioxoborolane) – 10,20 – diphenylporphyrin

Nuur Haziqah Mohd Radzuan, and Nawwar Hanun Abdul Malek, and Mohammad Fadzley Ngatiman, and Tan Ke Xin, and Mohd Bakri Bakar, and Nurul Izzaty Hassan, and Muntaz Abu Bakar, (2018) Synthesis and X-ray single crystal study of 5-(4,4,5,5 – tetramethyl – 1,3,2 –dioxoborolane) – 10,20 – diphenylporphyrin. Sains Malaysiana, 47 (9). pp. 2083-2090. ISSN 0126-6039


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Borylated porphyrin is one of building blocks in coupling reactions to obtain the multiporphyrin containing two, three or more subunits of porphyrins. In this study, one of borylated porphyrin derivatives, 5-(4,4,5,5 – tetramethyl – 1,3,2 – dioxoborolane) -10,20 – diphenylporphyrin (B-DPP) was synthesized through four steps of reactions. The building block of porphyrin, dipyrromethane was synthesized through a condensation reaction in the presence of trifluoroacetic acid as catalyst. Subsequently, A2B2 type of porphyrin was obtained by Lindsey condensation reaction followed by bromination reaction to produce porphyrin halide. Suzuki cross coupling reaction between porphyrin halide and pinacolborane with Pd (II) catalyst afforded 40% of borylayed porphyrin. The product was successfully characterized by using nuclear magnetic resonance spectroscopy (NMR) and UV-Visible spectroscopy (UV-Vis). This compound crystallized from a mixture of dichloromethane/methanol to give violet needle-like crystal. Crystallographic studies showed this compound crystallized in monoclinic system with space group of P21/c.

Item Type:Article
Keywords:Borylated porphyrin; Porphyrin; Suzuki cross coupling; X-ray structural study
Journal:Sains Malaysiana
ID Code:12397
Deposited By: ms aida -
Deposited On:05 Dec 2018 03:26
Last Modified:07 Dec 2018 23:30

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