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language
eng
Author
Saburo Neya
Description
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.
Subject
porphyrin
trifluoromethyl
alkoxycarbonyl
solvolysis
Journal Title
Molecules
Volume
21
Issue
252
Start Page
1
End Page
8
ISSN
1420-3049
Published Date
2016-02-23
DOI
Publisher
MDPI
NII Type
Journal Article
Format
PDF
Relation
Text Version
出版社版
Gyoseki ID
e29687
OAI-PMH Set
Faculty of Science and Engineering