TY - JOUR
T1 - Cyclo[6]pyridine[6]pyrrole
T2 - A dynamic, twisted macrocycle with no meso bridges
AU - Zhang, Zhan
AU - Cha, Won Young
AU - Williams, Neil J.
AU - Rush, Elise L.
AU - Ishida, Masatoshi
AU - Lynch, Vincent M.
AU - Kim, Dongho
AU - Sessler, Jonathan L.
PY - 2014/5/28
Y1 - 2014/5/28
N2 - A large porphyrin analogue, cyclo[6]pyridine[6]pyrrole, containing no meso bridging atoms, has been synthesized through Suzuki coupling. In its neutral form, this macrocycle exists as a mixture of two figure-eight conformers that undergo fast exchange in less polar solvents. Upon protonation, the dynamic twist can be transformed into species that adopt a ruffled planar structure or a figure-eight shape depending on the extent of protonation and counteranions. Conversion to a bisboron difluoride complex via deprotonation with NaH and treatment with BF3 acts to lock the macrocycle into a figure-eight conformation. The various forms of cyclo[6]pyridine[6]pyrrole are characterized by distinct NMR, X-ray crystallographic, and spectroscopic features.
AB - A large porphyrin analogue, cyclo[6]pyridine[6]pyrrole, containing no meso bridging atoms, has been synthesized through Suzuki coupling. In its neutral form, this macrocycle exists as a mixture of two figure-eight conformers that undergo fast exchange in less polar solvents. Upon protonation, the dynamic twist can be transformed into species that adopt a ruffled planar structure or a figure-eight shape depending on the extent of protonation and counteranions. Conversion to a bisboron difluoride complex via deprotonation with NaH and treatment with BF3 acts to lock the macrocycle into a figure-eight conformation. The various forms of cyclo[6]pyridine[6]pyrrole are characterized by distinct NMR, X-ray crystallographic, and spectroscopic features.
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U2 - 10.1021/ja503451m
DO - 10.1021/ja503451m
M3 - Article
AN - SCOPUS:84901704511
SN - 0002-7863
VL - 136
SP - 7591
EP - 7594
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 21
ER -