期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 19, 页码 5780-5793出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200702028
关键词
crystallography; long bonds; redox chemistry; strained molecules; through-bond interactions
Acenapthalene, pyracene, and dihydropyracylene attached to two units of spiroacridan are a novel class of hexaphenylethane (HPE) derivatives that have an ultralong C-sp3-C-sp3 bond (1.77-1.70 angstrom). These sterically challenged molecules were cleanly prepared by C-C bond formation through two-electron reduction from the less-hindered dications. These ultralong bonds were realized based on several molecular-design concepts including enhanced front strain through multiclamping by means of fusing or bridging aryl groups in the HPE molecule. The lengths of these ultralong bonds and their relation to the conformation (torsional angle) were also validated by means of theoretical calculations. Bond-fission experiments revealed that the bonds are more easily cleaved than standard covalent bonds to produce the corresponding dication upon oxidation with an increase in the length of the C-C bond.
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