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Conformational Preference in Bis(porphyrin) Tweezer Complexes: A Versatile Chirality Sensor for α‐Chiral Carboxylic Acids
Author(s) -
Tanasova Marina,
Borhan Babak
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200147
Subject(s) - chemistry , porphyrin , chirality (physics) , circular dichroism , linker , molecular tweezers , stereochemistry , tweezers , molecule , structural rigidity , supramolecular chemistry , photochemistry , organic chemistry , chiral symmetry , physics , geometry , quantum mechanics , mathematics , computer science , nambu–jona lasinio model , quark , operating system
Metallated porphyrin tweezers have demonstrated a remarkable ability to function as reporters of absolute stereochemistry for a number of different classes of organic molecules. Flexibility in binding, however, can result in an ensemble of different Exciton Coupled Circular Dichroism (ECCD) active conformations that could lead to variable results. Linker flexibility was found to be a key determinant of binding conformation. Experimental results indicate that a balance between linker flexibility and rigidity could yield an optimum porphyrin tweezer that stabilizes a common conformation for all bound chiral guests. This leads to a more simplified approach to absolute stereochemical determination of asymmetry for small organic molecules. This was demonstrated by the use of a C 3 ‐linked zincated porphyrin tweezer that yields a common conformational preference for a variety of α‐chiral carboxylic acids derivatized with a diamine carrier.