Sains Malaysiana, 2018;47:2083-2090.

Abstract

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, A2
B2 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.