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meso ‐Functionalization of Boron(III) Subporphyrin with Boron(III) meso ‐Lithiosubporphyrin
Author(s) -
Bekki Yosuke,
Shimizu Daiki,
Fujimoto Keisuke,
Osuka Atsuhiro
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802339
Subject(s) - chemistry , boron , benzophenone , lithium (medication) , electrophile , medicinal chemistry , electrochemistry , halogenation , polymer chemistry , photochemistry , organic chemistry , catalysis , medicine , electrode , endocrinology
Boron(III) meso ‐lithiosubporphyrin was prepared by bromine–lithium exchange of B‐tolyl B III meso ‐bromosubporphyrin with n ‐butyllithium at −98 °C. The resulting subporphyrinyllithium was treated with various electrophiles such as benzophenone, N , N ‐dimethylformamide, CO 2 , chlorotrimethylsilane, N ‐fluorobenzenesulfonimide, and dimesitylboryl fluoride to give the corresponding meso ‐functionalized B III subporphyrins. The nucleophile was also used to construct B III subporphyrin dimers such as bis(B III subporphyrinyl)ketone, bis(B III subporphyrinyl)carbinol, and disilane‐bridged B III subporphyrin dimer. The structural, optical, and electrochemical properties of these meso ‐functionalized B III subporphyrins were examined by UV/Vis absorption and fluorescence spectroscopy, electrochemical studies, and DFT calculations.