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, Nawwar Hanun Abdul Malek, Mohammad Fadzley Ngatiman, Tan Ke Xin, Mohd Bakri Bakar, Nurul Izzaty Hassan, Muntaz Abu Bakar

Research output: Contribution to journalArticle

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, 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.

Original languageEnglish
Pages (from-to)2083-2090
Number of pages8
JournalSains Malaysiana
Volume47
Issue number9
DOIs
Publication statusPublished - 1 Jan 2018

Fingerprint

Porphyrins
Single crystals
X rays
Condensation reactions
Trifluoroacetic Acid
Catalysts
Methylene Chloride
Ultraviolet spectroscopy
Needles
Nuclear magnetic resonance spectroscopy
Methanol
Derivatives
Crystals

Keywords

  • Borylated porphyrin
  • Porphyrin
  • Suzuki cross coupling
  • X-ray structural study

ASJC Scopus subject areas

  • General

Cite this

Synthesis and X-ray single crystal study of 5-(4,4,5,5 – tetramethyl – 1,3,2 – dioxoborolane) – 10,20 – diphenylporphyrin. / Radzuan, Nuur Haziqah Mohd; Malek, Nawwar Hanun Abdul; Ngatiman, Mohammad Fadzley; Xin, Tan Ke; Bakar, Mohd Bakri; Hassan, Nurul Izzaty; Abu Bakar, Muntaz.

In: Sains Malaysiana, Vol. 47, No. 9, 01.01.2018, p. 2083-2090.

Research output: Contribution to journalArticle

Radzuan, Nuur Haziqah Mohd ; Malek, Nawwar Hanun Abdul ; Ngatiman, Mohammad Fadzley ; Xin, Tan Ke ; Bakar, Mohd Bakri ; Hassan, Nurul Izzaty ; Abu Bakar, Muntaz. / Synthesis and X-ray single crystal study of 5-(4,4,5,5 – tetramethyl – 1,3,2 – dioxoborolane) – 10,20 – diphenylporphyrin. In: Sains Malaysiana. 2018 ; Vol. 47, No. 9. pp. 2083-2090.
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AU - Malek, Nawwar Hanun Abdul

AU - Ngatiman, Mohammad Fadzley

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AB - 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.

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