This monograph focuses on the principles of supramolecular complexation and catalysis rather than serve as an encyclopedia for all the cyclophanes prepared for molecular recognition studies. It should provide a state-of-the-art view on the intermolecular forces that hold together supramolecular complexes of cyclophanes with neutral and charged organic molecules in the liquid phase. Many studies in this monograph specifically demonstrate the characteristics and advantages of bridged aromatic compounds as receptors. To provide the space for an in-depth discussion of the principles of molecular recognition, cyclophane synthesis has been almost entirely omitted. Among the 650 literature references in this volume, more than 360 refer to publications that appeared between 1985 and 1990.
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978-0-85186-405-1 (9780851864051)
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Schweitzer Klassifikation
Part 1 From ansa compounds to paracyclophane to cyclophane complexes: the origins of cyclophane chemistry; molecular shape - an experimental calibration of the space occupancy of atoms and functional groups; probing weak non-covalent interactions between chromophores in rigid, geometrically defined cyclophane frames; modelling interactions and reactions in biological systems - stereochemical control imposed by cyclophane skeletons; cyclophane complexation - from n-n to inclusion complexes. Part 2 Inclusion complexes of neutral molecules in aqueous solution: the fist cyclophanes for the inclusion of apolar substrates; structures of cyclophane receptors for apolar inclusion complexation; aggregation behaviour of cyclophanes in aqueous solution; complexes of polycyclic aromatic hydrocarbons; complexes of naphthalene derivatives; complexes of benzene derivatives; complexes of heteroaromatic substrates; complexes of aliphatic substrates. Part 3 Apolar complexation in organic solvents: complexation of polycyclic arenes; structural factors determining the complexation strength; the strength of molecular complexation of arenes in water and in organic solvents is predictable by linear free energy relationships; electron donor-acceptor interactions stabilize inclusion complexes of aromatic guests; the cryptophanes - shape -selective inclusion complexation of methane derivatives; from cavitands to hemicarcerands to carcerands - increasing the barriers for escape of encapsulated organic molecules; apolar complexation strength in binary solvent mixtures. Part 4 Cyclophane complexes of charged organic guests: high guest selectivity in the inclusion; ion-dipole effect as a force for molecular recognition; attractive coulombic interactions at the origin of molecular cation and molecular anion complexation; cyclophane subunits as apolar binding sites in polytopic receptors; from second sphere coordination to catenane formation; azaparacyclophanes at the interface between molecular receptors and micellar aggregates. Part 5 Hydrogen-bonded complexes of cyclophanes and small neutral molecules: small neutral molecule binding to crowns and benzo-annelated derivatives; concave functionality - cyclophanes for phenol complexation; carbohydrate complexation by an octahydroxy metacyclophane; cyclophanes for nucleotide base recognition; barbiturate receptors; imidazole recognition - a remarkable relation between solvent size and complexation strength. (Part contents)
