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Synthesis of dihydroxyoligophenylenes containing π-deficient or π-excess hetero-aromatic rings and their solvatochromic behavior

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
66
Issue
34
Identifiers
DOI: 10.1016/j.tet.2010.06.087
Keywords
  • Dihydroxyoligophenylene
  • Suzuki Coupling
  • Hetero-Aromatic Ring
  • Photoluminescence
  • Solvatochromism

Abstract

Abstract Dihydroxyoligophenylenes ( HO-ArPh( m)-OH s) with 9,9-dihexyl-2,7-fluorene (Ar=Flu), 2,5-dioctyloxy-1,4-benzene (Ar=Dob), pyridine (Ar=Py), or thiophene (Ar=Th) rings were synthesized by the Suzuki coupling reaction. Absorption maxima ( λ max) of HO-ArPh( m)-OH s shifted progressively toward long wavelengths due to the expansion of the π-conjugation system with an increase in the number of benzene rings. Deprotonation of the OH groups of HO-ArPh( m)-OH s by treatment with NaH caused a bathochromic shift of λ max. The bathochromic shift of the deprotonated species increased with the donor numbers (DNs) of the solvents. The emission peak positions of NaO-ArPh( m)-ONa s depended on the DNs of the solvents; therefore, the emission color could be tuned by changing the solvent.

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