Expanded Bacteriochlorins


  • Financial support from the NSF (CHE-0517782 and CHE-1058846 to C.B. and an REU fellowship to S.W.) is gratefully acknowledged. The X-ray diffractometer was funded by NSF Grant 0087210, Ohio Board of Regents Grant CAP-491, and by Youngstown State University.


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Ruffled rings: Both pyrrolidine moieties in meso-tetraaryl-7,8,17,18-tetrahydroxybacteriochlorins can be sequentially expanded into morpholine rings to give the first bacteriochlorin-like derivatives containing two non-pyrrolic heterocycles. These porphyrioids are characterized by nonplanar conformations and significantly red-shifted optical spectra, both of which can be modulated by the introduction of linkages between β and o-phenyl positions.