Rapid Synthesis of Alkyloxy Porphyrins Under Microwave Irradiation

Abstract

Alkyloxy porphyrins have been prepared by direct coupling of 5-para-hydroxyphenyl-10,15,20-triphenylporphyrin and alkyl halides under microwave irradiation within several minutes. The length of the alkyl halides has no obvious effect on the yields and reaction time; however, the steric structure of the alkyl halides has a great impact on the reaction time. All the products were confirmed by ¹H NMR.

Keywords:

• Alkyl halide
• alkyloxy porphyrin
• ether
• microwave
• Williamson

ACKNOWLEDGMENTS

The authors thank the prophase research of National Key Basic Research Development Plan of China (2005CCA01400), the National Natural Science Foundation of China (20776053), and the Program for New Century Excellent Talents in University (NCET-06–740) for providing financial support for this project.

Notes

^a Reaction conditions: 0.16 mmol (0.1 g) HOPTPP, 1.6 mmol dodecyl bromide, 20 mL DMF, 2 g anhydrous K₂CO₃, 3 min.

^b All yields refer to isolated product which were characterized by ¹H NMR data.

^c Reaction conditions: 8 mL DMF, 5.0 mmol (2 g) NaOH, 0.179 mmol (0.113 g) HOPTPP, 0.458 mmol (0.114 g) dodecyl bromide, room temperature, 3 h.

^a Reaction conditions: 0.16 mmol (0.1 g) HPTPP, 1.6 mmol alkyl halide, 20 mL DMF, and 2 g anhydrous K₂CO₃, 300 W power.

^b All yields refer to isolated products, which were characterized by¹H NMR data.

^c Reaction conditions: 4.3 mmol (2.73 g) HOPTPP, 100 mL DMF, 0.065 mol (14 g) 1, 4-dibromobutane, 9 g anhydrous K₂CO₃, room temperature, 36 h.

^d 8 mL DMF, 0.2 g (5.0 mmol) NaOH, 0.1 13 g (0.179 mmol) HOPTPP,0.114 g (0.458 mmol) of dodecyl bromide, room temperature, 3 h.

^e 0.25 mmol (0.158 g) HOPTPP, 30 mL DMF, 80.°C, 1 mL hexadecyl bromide, 3 h.