Abstract
A novel π-stacked polymer based on a pseudo–meta–linked [2.2]paracyclophane moieties was synthesized by Sonogashira-Hagihara coupling. The UV-vis absorption spectra of the synthesized polymer and model compounds revealed an extension of the conjugation length owing to the through-space conjugation. The optical properties of the π-stacked dimer with the pseudo–meta–linked [2.2]paracyclophane unit were compared with those of the corresponding dimers with the pseudo–ortho– and pseudo–para–linked [2.2]paracyclophane units.
Highlights
A novel π-stacked polymer based on a pseudo–meta–linked [2.2]paracyclophane moieties was synthesized by Sonogashira-Hagihara coupling
Our interests have focused on the unique structures of [2.2]paracyclophane, repeatedly incorporating their molecular skeletons into π-conjugated polymer backbones through the use of disubstituted [2.2]paracyclophane compounds as comonomers [5,6,7,8,9,10]
Akita and coworkers reported the synthesis of m-3 from m-2 by the Sonogashira-Hagihara coupling using the PdCl2 (PPh3 )2 /CuI catalytic system (33%) and the removal of TMS groups with Bu4 NF to obtain m-4 (79%) [18]; the total yield of m-4 from m-2 was 26%
Summary
A novel π-stacked polymer based on a pseudo–meta–linked [2.2]paracyclophane moieties was synthesized by Sonogashira-Hagihara coupling. The UV-vis absorption spectra of the synthesized polymer and model compounds revealed an extension of the conjugation length owing to the through-space conjugation. The [2.2]paracyclophane unit provided a void space in the conjugated polymer main chain, leading to a partly π-stacked structure. The UV-vis absorption spectra of the corresponding oligomers as well as polymers with various molecular weights were red-shifted as the number of stacked π-electron systems increased [10]. We named this class of π-stacked polymers “through-space conjugated polymers”. After the successful development of an optical resolution method [11], we synthesized optically active through-space conjugated polymers [12,13]
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