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Photophysical Studies on the Interaction of Formamide and Alkyl Substituted Amides with Photoinduced Electron Transfer (PET) Based Acridinedione Dyes in Water

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Abstract

Interaction of photoinduced electron transfer (PET) based acridinedione dye (ADR 1) with amides like formamide, acetamide and dimethylformamide (DMF) were investigated by fluorescence spectral techniques. A fluorescence enhancement accompanied with a blue shift in the emission maximum was observed on the addition of amides to ADR 1 dye, which possess C6H4(p-OCH3) in the 9th position of the basic acridinedione ring. The extent of fluorescence enhancement and the blue shift in the emission maximum of ADR 1 dye is of the order of DMF > acetamide > formamide. DMF, which is more hydrophobic and less polar, results in a higher extent of fluorescence enhancement and a larger shift in the emission maximum towards the blue region. On the addition of amides, the ADR 1 dye prefers to orient towards a more hydrophobic phase surrounded by more number of amide molecules. The fluorescence enhancement of ADR 1 dye is attributed to the suppression of PET process occurring through space. The influence of the hydrophobic nature and the polarity of the amides on the excited state properties of acridinedione dyes are elucidated by steady-state and time resolved fluorescence measurements.

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Acknowledgements

Financial support by DST-IRHPA and UGC-INNOVATIVE Programme is acknowledged. R.K thanks the UGC for providing the financial assistance.

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Authors and Affiliations

  1. National Centre for Ultrafast Processes, University of Madras, Taramani Campus, Chennai, 600 113, India

    R. Kumaran & P. Ramamurthy

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  1. R. Kumaran
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  2. P. Ramamurthy
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Correspondence to P. Ramamurthy.

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Figure S1

Absorption spectra of ADR 2 dye in the absence and presence of formamide in water. 1) ADR 1 dye alone (1.5 × 10−5 M), 2) formamide 2.5 M, 3) ADR 1 dye + formamide 2.5 M, 4) ADR 1 dye + formamide 5.0 M (JPEG 21 kb)

High Resolution Image (TIFF 14 kb)

Figure S2

Emission spectra of ADR 1 dye in the absence and presence of acetamide in water λex378 nm. 1) ADR 1 dye alone (1.5 × 10−5 M), 2) ADR 1 dye + acetamide 2.5 M, 3) ADR 1 dye + acetamide 5.0 M, 4) ADR 1 dye + acetamide 7.5 M, 5) ADR 1 dye + acetamide 10.0 M, 6) ADR 1 dye + acetamide 12.5 M (JPEG 20 kb)

High Resolution Image (TIFF 13 kb)

Figure S3

Fluorescence decay of ADR 1 and ADR 2 dyes in water. λex378 nm (JPEG 28 kb)

High Resolution Image (TIFF 17 kb)

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Kumaran, R., Ramamurthy, P. Photophysical Studies on the Interaction of Formamide and Alkyl Substituted Amides with Photoinduced Electron Transfer (PET) Based Acridinedione Dyes in Water. J Fluoresc 21, 2165–2172 (2011). https://doi.org/10.1007/s10895-011-0918-z

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  • DOI: https://doi.org/10.1007/s10895-011-0918-z

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