Synthesis of C3 benzo[1,2-e:3,4-e':5,6-e"]tribenzo[l]acephenanthrylenes ("crushed fullerene" derivatives) by intramolecular palladium-catalyzed arylation

The C60 polyarenes 4, 5, 18 a, and 18 b have been synthesized from truxene by triple alkylation at C5, C10, and C15 followed by a palladium-catalyzed intramolecular arylation. The synthesis of "crushed fullerene" C60H30 (2) is the most efficient reported to date and proceeds in 33% overall yield.     

Theoretical study of racemization in chiral alkenylidene truxenes

DFT based methods have been used to study the racemization process of chiral truxene derivatives. Four minima and the transition state connecting them have been characterized. It has been found that the energetic results for the transition states are correlated for each compound and also among the different systems considered. Thus, a unique equation has been found to fit all the values obtained. Model systems have shown that the calculated barriers are not inherent to the truxene structure. The AIM analysis has shown the presence of a large number of intramolecular closed‐shell interactions while electron density and Laplacian at the bond critical points are exponentially correlated with the interatomic distance. Copyright © 2008 John Wiley & Sons, Ltd.     

Rigid Conjugated Twisted Truxene Dimers and Trimers as Electron Acceptors

A new class of rigid twisted truxenone oligomers with an enlarged π backbone has been established by oxidative dimerization reactions. The resulting extended conjugated systems have large extinction coefficients and low‐lying LUMO levels and show good solubility in common organic solvents, thus making them attractive compounds as new electron acceptors in organic electronics. Their suitability as electron acceptors has been demonstrated in bulk‐heterojunction organic solar cells with poly({4,8‐bis[(2‐ethylhexyl)oxy]benzo[1,2‐b:4,5‐b′]dithiophene‐2,6‐diyl}{3‐fluoro‐2‐[(2‐ethylhexyl)carbonyl]thieno[3,4‐b]thiophenediyl}) (PTB7) as the donor material.