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    Gram-Scale Syntheses and Conductivities of [10]Cycloparaphenylene and Its Tetraalkoxy Derivatives

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    [10]­Cycloparaphenylene ([10]­CPP) and its tetraalkoxy derivatives were synthesized on the gram scale in 7 steps starting from 1,4-benzoquinone or 2,5-dialkoxy-1,4-benzoquinone. The key steps involve the highly <i>cis</i>-selective bis-addition of 4-bromo-4′-lithiobiphenyl to the quinones to produce a five-ring unit containing cyclohexa-1,4-diene-3,6-diol moiety, the platinum-mediated dimerization of the five-ring unit, and the H<sub>2</sub>SnCl<sub>4</sub>-mediated reductive aromatization of cyclohexadienediol. The tetraalkoxy substituents increased the solubility of [10]­CPP in common organic solvents. The carrier-transport properties of thin films of [10]­CPP and its derivatives were measured for the first time and indicated that [10]­CPP derivatives could rival phenyl-C<sub>61</sub>-butyric acid methyl ester, which is used widely as an <i>n</i>-type active layer in bulk heterojunction photovoltaics
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