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Bay Functionalized Perylenediimide with Pyridine Positional Isomers: NIR Absorption and Selective Colorimetric/Fluorescent Sensing of Fe3+ and Al3+ Ions

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Abstract

Bay functionalized perylene diimide substituted with pyridine isomers, (2-pyridine (2HMP-PDI), 3-pyridine (3-HMP-PDI) and 4-pyridine (4-HMP-PDI)) have been synthesized and explored for selective coloro/fluorimetric sensing of heavy transition metal ions. HMP-PDIs showed strong NIR absorption (760–765 nm) in DMF. The absorption and fluorescence of HMP-PDIs have been tuned by make use of pyridine isomers. Reddish-orange color was observed for 2-HMP-PDI (λmax = 437, 551, 765 nm) whereas 4-HMP-PDI exhibited light green (λmax = 432, 522, 765 nm). 3-HMP-PDI showed orange-yellow (λmax = 431, 524, 762 nm). The fluorescence spectra of 2-, 3- and 4-HMP-PDI showed λmax at 585, 538, 546 nm, respectively. Interestingly, HMP-PDI dyes showed selective color change (intense pink color) and fluorescence quenching for Fe3+ and Al3+ metal ions in DMF. Absorbance spectra revealed complete disappearance of NIR absorption and intensification/appearance of new peak at lower wavelength. The concentration dependent studies suggest that 4-HMP-PDI can detect up to 36.52 ppb of Fe3+ and 43.12 ppb of Al3+ colorimetrically. The interference studies in presence of other metal ions confirmed the good selectivity for Fe3+ and Al3+. The mechanistic studies indicate that Lewis acidic character of Fe3+ and Al3+ ions were responsible for selective color change and fluorescence quenching.

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Acknowledgements

Financial support from the Science and Engineering Research Board (SERB), New Delhi, India (SERB No. EMR/2015/00-1891, SB/FT/CS-182/2011) is acknowledged with gratitude. VM is grateful to UGC, Government of India for UGC research award-2014-16 (No: 30-11/2015 (SA-II). The CRF facility of SASTRA University is also acknowledged for absorption spectroscopy.

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Authors and Affiliations

  1. School of Chemical & Biotechnology, SASTRA University, Thanjavur, Tamil Nadu, 613401, India

    Anu Kundu & Savarimuthu Philip Anthony

  2. Department of Chemistry, Karunya University, Coimbatore, Tamil Nadu, 641 114, India

    Jayaraman Pitchaimani & Vedichi Madhu

  3. Materials Chemistry Division, School of Advanced Science, VIT University, Vellore, 632014, India

    Pachagounder Sakthivel & Ramasamy Ganesamoorthy

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  1. Anu Kundu
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  2. Jayaraman Pitchaimani
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  3. Vedichi Madhu
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  6. Savarimuthu Philip Anthony
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Correspondence to Vedichi Madhu or Savarimuthu Philip Anthony.

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Kundu, A., Pitchaimani, J., Madhu, V. et al. Bay Functionalized Perylenediimide with Pyridine Positional Isomers: NIR Absorption and Selective Colorimetric/Fluorescent Sensing of Fe3+ and Al3+ Ions. J Fluoresc 27, 491–500 (2017). https://doi.org/10.1007/s10895-016-1976-z

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