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Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin

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Abstract

The riboflavin dye 2,3,4,5-tetra-O-acetyl-1-[3-(6-bromohexyl)-7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-1-deoxypentitol and its pyridinium salt were synthesized, and studied by absorption and fluorescence spectroscopy in solutions and on thin film states. The first absorption band of riboflavin-pyridinium salt derivative is red-shifted by 10 nm compared to neutral one on film. Cationic riboflavin derivative shows significant wavelength changes on its fluorescence emission spectrum in the excited state depending on the solvent polarity and the electronic environment. The fluorescence quantum yields of cationic riboflavin gave much higher values as compared to that of its neutral form. The fluorescence lifetimes were found to be in the range of 5.5–6.6 ns with mono − exponential behavior. These dyes possess low-lying HOMO energy levels which are suitable to be able to inject holes to donor polymers so that they can be used as acceptor component in the active layer of bulk heterojunction solar cells (BHJ-SCs). Photovoltaic responses are reported for P3HT:riboflavin active layer wherein the synthesized dyes are used as acceptor component. Also, neutral riboflavin shows greater electron mobility value of 1.3 × 10−3 cm2/V∙s compared to its cationic derivative.

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Acknowledgements

This work was supported by the Scientific and Technological Research Council of Turkey (TUBITAK) with the project number of 113Z250. We thank to Ege University for the support of the use of Gaussian 09 W programme for DFT calculations.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Arts and Science, Manisa Celal Bayar University, Yunus Emre, 45140, Manisa, Turkey

    Gözde Murat Saltan & Haluk Dinçalp

  2. Solar Energy Institute, Ege University, Bornova, 35100, Izmir, Turkey

    Deniz Aykut Kıymaz & Ceylan Zafer

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  1. Gözde Murat Saltan
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  2. Deniz Aykut Kıymaz
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  4. Haluk Dinçalp
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Correspondence to Haluk Dinçalp.

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Saltan, G.M., Kıymaz, D.A., Zafer, C. et al. Comparison of the Optoelectronic Performance of Neutral and Cationic Forms of Riboflavin. J Fluoresc 27, 1975–1984 (2017). https://doi.org/10.1007/s10895-017-2135-x

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  • DOI: https://doi.org/10.1007/s10895-017-2135-x

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