Molecular recognition with C-clamp porphyrins: synthesis, structural, and complexation studies.
Porphyrin-based molecular clefts equipped with a strategically positioned carboxylic group have been synthesized. These ditopic porphyrins exhibit excellent binding affinity for many neutral substrates. X-ray structures of a porphyrin-water inclusion complex and a Zn(porphyrin)-methanol complex reveal how the carboxylic group interacts with substrates via H-bonding. Multipoint recognition is demonstrated in the differential binding of 1,2,3- versus 1,2,4-triazole, suggesting the possible use of such receptors to separate heterocyclic bases.
Liang
Y
Y
Department of Chemistry, Michigan State University, East Lansing 48824, USA.
Chang
C K
CK
Peng
S M
SM
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008665:Metalloporphyrins / Q000737:chemistry / Q000378:metabolism; D008670:Metals / Q000378:metabolism; D008956:Models, Chemical; D008958:Models, Molecular; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D013379:Substrate Specificity; D014230:Triazoles / Q000737:chemistry
D008665:Metalloporphyrins; D008670:Metals; D011166:Porphyrins; D014230:Triazoles; C103211:naphthalene Kemp's acid porphyrin; C017802:zinc hematoporphyrin