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Issue 33, 2013
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Comparison of 1,4-distyrylfluorene and 1,4-distyrylbenzene analogues: synthesis, structure, electrochemistry and photophysics

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Abstract

A series of nine 1,4-distyrylfluorene derivatives (2) functionalized with substituents of variable electron-donating or -accepting capabilities was synthesised. The photophysical properties of the molecules were investigated, including UV/vis absorption, photoluminescence emission, and fluorescence quantum yields. Photophysical properties of chromophores 2 were found to exhibit significant solvatochromic effects, especially in the Stokes shift and photoluminescence maxima. The electrochemical properties of series 2 were also assessed by cyclic voltammetry and differential pulse voltammetry. Results of photophysical and electrochemical analyses were further supported by DFT calculations (B3LYP/6-31G*) and single crystal X-ray diffraction on select molecules. The contributions of intermolecular π-stacking and hydrogen bonding to crystal packing are discussed. A series of nine 1,4-distyrylphenylene derivatives (3) were also synthesised and similarly characterized for comparison to photophysical and solvatochromic effects observed in series 2. Properties of similarly-substituted molecules in series 2 and 3 were compared to one another in order to assess the influence of the 1,4-fluorenylene unit.

Graphical abstract: Comparison of 1,4-distyrylfluorene and 1,4-distyrylbenzene analogues: synthesis, structure, electrochemistry and photophysics

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Supplementary files

Article information


Submitted
24 Mar 2013
Accepted
23 Jun 2013
First published
18 Jul 2013

Org. Biomol. Chem., 2013,11, 5425-5434
Article type
Paper

Comparison of 1,4-distyrylfluorene and 1,4-distyrylbenzene analogues: synthesis, structure, electrochemistry and photophysics

B. J. Laughlin, T. L. Duniho, S. J. El Homsi, B. E. Levy, N. Deligonul, J. R. Gaffen, J. D. Protasiewicz, A. G. Tennyson and R. C. Smith, Org. Biomol. Chem., 2013, 11, 5425
DOI: 10.1039/C3OB40580J

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