Synthesis and characterization of ethylene glycol substituted poly(phenylene Vinylene) derivatives

Chun Chih Wang, Hsinhan Tsai, Hung Hsin Shih, Seaho Jeon, Zhihua Xu, Darrick Williams, Srinivas Iyer, Timothy C. Sanchez, Leeyih Wang, Mircea Cotlet, Hsing Lin Wang

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

We report the synthesis of a series of water-soluble, fluorescent, conjugated polymers via the Gilch reaction with an overall yield greater than 40%. The yield for the Gilch reaction decreases with the increase in the length of the side chain (ethylene glycol repeat units), presumably due to the steric effects inhibiting the linking of monomeric units. The hydrophilic side chain enhances the solubility of the polymer in water and concomitantly leads to a side-chain-dependent conformation and solvent-dependent quantum efficiency. An increase in the ethylene glycol repeat units on the polymer side chain structure results in changes in chain packing; hence, the crystallinity evolves from semicrystalline to liquid crystalline to completely amorphous. An increase in the length of the side chain leads to changes in the polymer?solvent interaction as manifested in the photophysical properties of these polymers. These novel polymers exhibit two glass transition temperatures, which can be readily rationalized by differences in microstructure when casted from hydrophobic and hydrophilic solvents. Cyclic voltammograms of polymer 1d?3d suggest two-electron transfer, as compared to P1 which has one complete redox pair. The potential of having a nanoscaled domain structure and stabilizing two electrons on a polymer chain signifies the potential of these polymers in fabricating electronic and photovoltaic devices.

Original languageEnglish (US)
Pages (from-to)738-747
Number of pages10
JournalACS Applied Materials and Interfaces
Volume2
Issue number3
DOIs
StatePublished - Mar 24 2010

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Ethylene Glycol
Ethylene glycol
Polymers
Derivatives
Electrons
Water
Conjugated polymers
Quantum efficiency
Conformations
Solubility
Crystalline materials
Microstructure
Liquids

Keywords

  • Conjugated polymer
  • Optical properties
  • Photophysics
  • Redox
  • Synthesis

Cite this

Synthesis and characterization of ethylene glycol substituted poly(phenylene Vinylene) derivatives. / Wang, Chun Chih; Tsai, Hsinhan; Shih, Hung Hsin; Jeon, Seaho; Xu, Zhihua; Williams, Darrick; Iyer, Srinivas; Sanchez, Timothy C.; Wang, Leeyih; Cotlet, Mircea; Wang, Hsing Lin.

In: ACS Applied Materials and Interfaces, Vol. 2, No. 3, 24.03.2010, p. 738-747.

Research output: Contribution to journalArticle

Wang, CC, Tsai, H, Shih, HH, Jeon, S, Xu, Z, Williams, D, Iyer, S, Sanchez, TC, Wang, L, Cotlet, M & Wang, HL 2010, 'Synthesis and characterization of ethylene glycol substituted poly(phenylene Vinylene) derivatives', ACS Applied Materials and Interfaces, vol. 2, no. 3, pp. 738-747. https://doi.org/10.1021/am900766s
Wang, Chun Chih ; Tsai, Hsinhan ; Shih, Hung Hsin ; Jeon, Seaho ; Xu, Zhihua ; Williams, Darrick ; Iyer, Srinivas ; Sanchez, Timothy C. ; Wang, Leeyih ; Cotlet, Mircea ; Wang, Hsing Lin. / Synthesis and characterization of ethylene glycol substituted poly(phenylene Vinylene) derivatives. In: ACS Applied Materials and Interfaces. 2010 ; Vol. 2, No. 3. pp. 738-747.
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