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Photophysical and Electrochemical Studies of 4-Dicyanomethylene 2,6-Dimethyl-4H-Pyran (DDP) Dye with Amides in Water

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Abstract

Photophysical and electrochemical studies of DDP dye with Formamide and alkyl substituted amides were carried out in water. Addition of Formamide (F), Acetamide (ACM), N,N-Dimethylformamide (DMF), Dimethylacetamide (DMAC) to DDP dye result in an isosbestic point. A fluorescence enhancement of DDP dye is observed on the addition of amides. Apart from the fluorescence enhancement, the addition of formamide result in no significant shift in the position of emission maxima of DDP dye whereas addition of ACM and DMF result in a shift towards the blue and red region respectively. DDP dye exhibits three lifetime components which are unique in lifetime and amplitude. The fluorescence lifetime and relative amplitude of DDP dye varies significantly by addition of amides in aqueous solution which are influenced by amidewater hydrogen-bonding network and hydrophobic influences of the alkyl substituted amides. The nature of interaction between dye and amide be predominantly through hydrogen-bonding wherein the carbonyl oxygen (C=O) of amides are bonded to N-H hydrogen of DDP dye through water molecule. The existence of more than one microenvironment of DDP dye in aqueous phase is elucidated by Electrochemical Impedence Spectroscopy (EIS) through Nyquist plots wherein it signifies that there exist at least three different micro environments which support the existence of different fluorescence lifetimes. Fluorescence spectral technique is used as an efficient tool to elucidate the nature of interaction of water soluble probe with hydrogen-bonding solutes is established in our studies.

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Acknowledgements

The authors are thankful to Prof. P. Ramamurthy and Dr.C.Selvaraju of National Centre for Ultrafast Processses, University of Madras, Chennai-600 113, India for permitting us to avail the fluorescence facilities. S.G and R.K thank Dr. Edamana Prasad, Associate Professor, Department of Chemistry, IIT Madras for permitting to avail the fluorescence lifetime facilities. The authors are thankful by, Shri Ashok Kumar Mundra The Secretary and Dr. R. Ganasen, The Principal and Dr. S. Ilangovan, former Head of the department of Chemistry Dwaraka Doss Goverdhan Doss Vaishnav College, Arumbakkam, Chennai-600 106 for their support and encouragement.

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  1. Department of Chemistry, Dwaraka Doss, Goverdhan Doss, Vaishnav College (Autonomous), 833, Gokul Bagh, E.V.R.Periyar Road, Arumbakkam, Chennai, Tamil Nadu, 600 106, India

    Somasundaram Gayathri, Rajaraman Vasanthi, Mahalingam Vanjinathan & Rajendran Kumaran

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  1. Somasundaram Gayathri
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  2. Rajaraman Vasanthi
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  3. Mahalingam Vanjinathan
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Correspondence to Rajendran Kumaran.

Electronic supplementary material

ESM 1

Absorption spectra of DDP dye (7.1 × 10−5 M) with ACM in water. 1) DDP dye (7.1 × 10−5 M), 2) DDP dye + ACM 2.0 M, 3) DDP dye + ACM 4.0 M, 4) DDP dye + ACM 6.0 M. (a) Isosbestic point. (PPTX 348 kb)

ESM 2

Absorption spectra of DDP dye (7.1 × 10−5 M) with DMF in water. 1) DDP dye (7.1 × 10−5 M), 2) DDP dye + DMF 2.0 M, 3) DDP dye + DMF 4.0 M, 4) DDP dye + DMF 6.0 M. (a) Isosbestic point. (PPTX 255 kb)

ESM 3

Absorption spectra of DDP dye (7.1 × 10−5 M) with DMAC in water. 1) DDP dye (7.1 × 10−5 M), 2) DDP dye + DMAC 2.0 M, 3) DDP dye + DMAC 4.0 M, 4) DDP dye + DMAC 6.0 M. (a) Isosbestic point. (PPTX 791 kb)

ESM 4

Fluorescence decay of DDP dye (7.1 × 10−5 M) as a function of ACM in water. λex 375 nm and λem 436 nm. 1)Laser profile. 2) DDP dye alone, 3) DDP dye + ACM 2.0 M, 4) DDP dye + ACM 4.0 M, 5) DDP dye + ACM 6.0 M. (PPTX 268 kb)

ESM 5

3D-Contor Spectrum of DDP dye (7.1 × 10−5 M) as a function of ACM in water λex375 nm and λem 436 nm. a) DDP dye + ACM 2.0 M, b) DDP dye + ACM 4.0 M, c) DDP dye + ACM 6.0 M. (PPTX 311 kb)

ESM 6

3D-Contor Spectrum of DDP dye (7.1 × 10−5 M) as a function of DMF in water λex375 nm and λem 436 nm. a) DDP dye + DMF 2.0 M, b) DDP dye + DMF 4.0 M, c) DDP dye + DMF 6.0 M, d) DDP dye + DMF 8.0 M, e) DDP dye + DMF 10.0 M. (PPTX 1238 kb)

ESM 7

3D-Contor Spectrum of DDP dye (7.1 × 10−5 M) as a function of DMAC in water λex375 nm and λem 436 nm. a) DDP dye + DMAC 2.0 M, b) DDP dye + DMAC 4.0 M, c) DDP dye + DMAC 6.0 M. (PPTX 833 kb)

ESM 8

Electrochemical Impedance Spectroscopy of DDP dye (7.1 × 10−5 M) With ACM (1.0 M) in water. (PPTX 272 kb)

ESM 9

Electrochemical Impedance Spectroscopy of DDP dye (7.1 × 10−5 M) With DMAC 1.0 M in water. (PPTX 260 kb)

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Gayathri, S., Vasanthi, R., Vanjinathan, M. et al. Photophysical and Electrochemical Studies of 4-Dicyanomethylene 2,6-Dimethyl-4H-Pyran (DDP) Dye with Amides in Water. J Fluoresc 28, 1379–1391 (2018). https://doi.org/10.1007/s10895-018-2303-7

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  • DOI: https://doi.org/10.1007/s10895-018-2303-7

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