Novel chiral poly(para‐phenylene) derivatives containing cyclophane‐type moieties

Abstract

The introduction of cyclic ansa-substituents allows for the synthesis of soluble poly-(para-pheny1ene)s PPPs possessing main chain chirality. The novel chiral PPP's represent an attractive combination of n-conjugated character and chirality. We have synthesized open chain (single-stranded) as well as ladder-type chiral PPPs. The singlestranded chiral PPP's exhibit temperature-dependent changes of chiroptical properties. The behaviour should be assigned to conformational changes. The chiral ladder polymers contain the cyclophane loops exclusively on one side of the molecular board and are characterized by an unexpectedly high chiroptical activity of the n-n*-transition. They are potential candidates to study non-linear chiroptical properties and to investigate circulary polarized luminescence (photo-and electroluminescence) effects.

Oligomers and Polymers Based on Bridged Phenylenes as Electronic Materials

“…A chiral LPPP has been prepared by using a resolved cyclophane bisboronic acid as one component in the initial Suzuki polycondensation. [49][50][51] Such a chiral polymer is a candidate for obtaining circularly polarized EL. A way to reduce defects through incomplete ring-closure is to replace the benzenebisboronic acid in Scheme 1 with a fluorenebisboronate.…”

Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials

“…10). Planarchiral compounds are structurally interesting and have potential as frameworks for functional materials such as chiral discriminators [80,81], chiral polymers and supramolecules [82,83], as well as guest receptors [84]. The rotation of the units leads to the exchange of conformers and racemization, so inhibiting the rotational motion is necessary for isolating planar-chiral pillar [5]arenes.…”

Aggregation-induced CD effects in chiral poly(2,5-dialkoxy-1,4-phenylene)s

“…In addition to our recently published approach of incorporating cyclic ansa-substituents in PPP-type macromolecules to induce a main chain chirality [17,18], we have also started a project to synthesize and investigate the properties of PPPs substituted with chiral alkoxy side chains. In this communication we describe the synthesis and (chir)optical properties of optically active poly(2,5bis[2-(S)-methylbutoxy]-1,4-phenylene) (BMB-PPP) (1).…”