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Molecules 2013, 18(6), 7035-7057; doi:10.3390/molecules18067035

Mirror-Symmetry-Breaking in Poly[(9,9-di-n-octylfluorenyl-2,7-diyl)-alt-biphenyl] (PF8P2) is Susceptible to Terpene Chirality, Achiral Solvents, and Mechanical Stirring

1
Graduate School of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, Nara 630-0192, Japan
2
Department of Materials Science and Engineering, University of California, Berkeley, CA 94720-1760, USA
*
Author to whom correspondence should be addressed.
Received: 13 May 2013 / Revised: 3 June 2013 / Accepted: 3 June 2013 / Published: 17 June 2013
(This article belongs to the Special Issue Asymmetric Catalysis)
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Abstract

Solvent chirality transfer of (S)-/(R)-limonenes allows the instant generation of optically active PF8P2 aggregates with distinct circular dichroism (CD)/circularly polarized luminescence (CPL) amplitudes with a high quantum yield of 16–20%. The present paper also reports subtle mirror-symmetry-breaking effects in CD-/CPL-amplitude and sign, CD/UV-vis spectral wavelengths, and photodynamics of the aggregates, though the reasons for the anomaly are unsolved. However, these photophysical properties depend on (i) the chemical natures of chiral and achiral molecules when used in solvent quantity, (ii) clockwise and counterclockwise stirring operations, and (iii) the order of addition of limonene and methanol to the chloroform solution.
Keywords: limonene; mirror symmetry breaking; polymer; chirality; optically active; circular dichroism; circularly polarized luminescence; vortex; parity violation; homochirality limonene; mirror symmetry breaking; polymer; chirality; optically active; circular dichroism; circularly polarized luminescence; vortex; parity violation; homochirality
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Fujiki, M.; Kawagoe, Y.; Nakano, Y.; Nakao, A. Mirror-Symmetry-Breaking in Poly[(9,9-di-n-octylfluorenyl-2,7-diyl)-alt-biphenyl] (PF8P2) is Susceptible to Terpene Chirality, Achiral Solvents, and Mechanical Stirring. Molecules 2013, 18, 7035-7057.

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