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Molecules 2016, 21(3), 252; doi:10.3390/molecules21030252

Synthesis of 5,10-bis(Trifluoromethyl) Substituted β-Octamethylporphyrins and Central-Metal-Dependent Solvolysis of Their meso-Trifluoromethyl Groups

1
Interdisciplinary Graduate School of Science and Engineering, Shimane University, 1060, Nishikawatsu-cho, Matsue, Shimane 690-8504, Japan
2
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan
*
Author to whom correspondence should be addressed.
Academic Editors: M. Graça P. M. S. Neves and M. Amparo F. Faustino
Received: 9 January 2016 / Revised: 15 February 2016 / Accepted: 19 February 2016 / Published: 23 February 2016
View Full-Text   |   Download PDF [951 KB, uploaded 23 February 2016]   |  

Abstract

5,10-Bistrifluoromethyl substituted β-octamethylporphyrins were synthesized via a scrambling side reaction of a dipyrromethane precursor in the presence of a large excess of trifluoroacetic acid. Compared with the trans-analogs, the cis-analogs of meso-trifluoromethyl β-octaalkylporphyrin showed more red-shifted absorption bands. These meso-trifluoromethyl derivatives of β-octaalkylporphyrins underwent smooth metalation, similar to other common porphyrins, however, the corresponding zinc complexes underwent a type of solvolysis, whereby the trifluoromethyl groups were converted into methoxycarbonyl groups by the methanol used as solvent. UV-visible absorption spectra and X-ray crystal structure analyses revealed that the presence of a methoxycarbonyl substituent did not influence the deformation of the molecular framework and its absorption properties; this is because the methoxycarbonyl has a planar and perpendicular geometry, as opposed to the relatively bulky trifluoromethyl substituent. View Full-Text
Keywords: porphyrin; trifluoromethyl; alkoxycarbonyl; solvolysis porphyrin; trifluoromethyl; alkoxycarbonyl; solvolysis
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Suzuki, M.; Neya, S.; Nishigaichi, Y. Synthesis of 5,10-bis(Trifluoromethyl) Substituted β-Octamethylporphyrins and Central-Metal-Dependent Solvolysis of Their meso-Trifluoromethyl Groups. Molecules 2016, 21, 252.

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