Synthesis of Triazole‐Bridged Unsymmetrical Porphyrin Dyads and Porphyrin–Ferrocene Conjugates

作者: Vijayendra S. Shetti , Mangalampalli Ravikanth

DOI: 10.1002/EJOC.200901070

关键词: Electron transferHeteroatomPorphyrinPolymer chemistryFerroceneChemistryPhotochemistryMetalloceneClick chemistryChemical synthesisAzide

摘要: A simple method has been used to synthesize four porphyrin azides with cores such as N4, N3S, N2SO and N2S2 in 60–90 % yields by treating the corresponding aminoporphyrins tert-butyl nitrite (tBuONO) azidotrimethylsilane (TMSN3) THF/CH3CN under mild reaction conditions. The hitherto unknown heteroatom were synthesized from their nitroporphyrins standard SnCl2/HCl reduction. azidoporphyrins six triazole-bridged unsymmetrical dyads containing two different types of sub-units well five porphyrin–ferrocene conjugates CuI-catalyzed “click” Various conditions studied best obtained CuI/DIPEA at room temperature for overnight. characterized various spectroscopic electrochemical techniques. In dyads, NMR, absorption studies indicate a weak interaction between sub-units. However, preliminary photophysical support an efficient singlet-singlet energy transfer one unit another reported here. conjugates, fluorescence was quenched significantly due photo-induced electron ferrocene porphyrin.

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