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Distinctive Chiral Conformations Induced to Poly (naphthalene-1,4-diyl) by Helix-sense-selective Polymerization and
Qingyu Wang1, Ka Son1, Adriana Pietropaolo2
1Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N21 W10, Kita-ku, Sapporo, 001-0021, Japan.
Abstract:
Optically active poly(naphthalene-1,4-diyl) was prepared through helix-sense-selective polymerization of the corresponding monomers and also through circularly polarized light (CPL) irradiation, resulting in distinctive circular dichroism (CD) spectral patterns. Chirality of the helix-sense-selective polymerization -based polymer is ascribed to preferred-handed helicity while that of the CPL-based polymer to a non-helical, chiral conformation ('biased-dihedral conformation') with preferred-handedness which was stable only in the solid state. The helix of the helix-sense-selective polymerization-based polymer gradually racemized in tetrahydrofuran while it was stabilized by aggregate formation in a hexane-dichloromethane solution. Both helix-sense-selective polymerization- and CPL-based polymers exhibited efficient circularly polarized luminescence.
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