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Benzodichalcogenophenes are functionalized at their termini via SN Ar reactions of their bismetalates with perfluoroarenes. The identities of X, Y, and W are varied to study the effects on LUMO energy levels and crystallization motif. X-ray crystallography reveals that nearly all new derivatives crystallize with coplanar ring systems within slipped 1D or 2D pi-stacks.
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Wang et al. (2008) studied this question.
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