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Gomez R, Segura JL, Martin N. Synthesis and characterization of novel optically active polyarylene vinylenes with controlled effective conjugation length. J Org Chem. 2000;65(22):7501-11doi: 10.1021/jo000761k.
Gomez, R., Segura, J. L., & Martin, N. (2000). Synthesis and characterization of novel optically active polyarylene vinylenes with controlled effective conjugation length. The Journal of organic chemistry, 65(22), 7501-11. https://doi.org/10.1021/jo000761k
Gomez, et al. "Synthesis and characterization of novel optically active polyarylene vinylenes with controlled effective conjugation length." The Journal of organic chemistry vol. 65,22 (2000): 7501-11. doi: https://doi.org/10.1021/jo000761k
Gomez R, Segura JL, Martin N. Synthesis and characterization of novel optically active polyarylene vinylenes with controlled effective conjugation length. J Org Chem. 2000 Nov 03;65(22):7501-11. doi: 10.1021/jo000761k. PMID: 11076608.
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J Org Chem. 2000 Nov 03;65(22):7501-11. doi: 10.1021/jo000761k.

Synthesis and characterization of novel optically active polyarylene vinylenes with controlled effective conjugation length.

The Journal of organic chemistry

Gomez, Segura, Martin

Affiliations

  1. Departamento de Quimica Organica, Facultad de Ciencias Quimicas, Universidad Complutense, E-28040 Madrid, Spain.

PMID: 11076608 DOI: 10.1021/jo000761k

Abstract

New chiral and soluble binaphthyl derivatives (12 and 13) endowed with carboxaldehyde or cyanomethyl functional groups have been prepared as suitable building blocks for the synthesis by Knoevenagel condensation of a series of optically active block copolymers (1-7) with controlled effective conjugation length. A variety of functionalized co-monomers (14-19) have been prepared by different synthetic procedures to be used in further polymerization reactions with binaphthyl derivatives 12 and 13. Depending upon the nature of the co-monomers, it is possible to tune the wavelength of the new polymers, which is very close to that of the respective repeating units. Fluorescence measurements on polymers 1-3 reveal a strong blue-green emission with Stokes shifts of 74-107 nm. Theoretical calculations at the semiempirical AM-1 level have been carried out on model compounds, and the calculated torsion angles are in agreement with the electronic spectra data. Finally, the redox properties of the polymers prepared (1-7) were determined by cyclic voltammetry, and an amphoteric behavior with oxidation potentials ranging from 1.1 to 1.6 V and reduction potentials close to -1.5 V was found.

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