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To facilitate the access to unique models for biological processes, we exam
ined six different synthetic routes to octi(p-phenylene) rods with lateral
and terminal substitutents R-L and R-T. This systematic study allowed us to
increase to overall yield for the synthesis of a new class of oligo(p-phen
ylene) ionophores about 20 times and to provide general insights into the p
racticability of synthetic routes to multiply substituted molecular rods.