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Issue 8, 2018
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Near infra-red dyes based on pyrene aza-BODIPYs

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Pyrene substituted donor–acceptor type NIR aza-BODIPYs were designed and synthesized. The 1,7-positions of the aza-BODIPY core were substituted by pyrene moieties and the 3,5-positions were substituted with phenyl/2-thienyl or anisyl groups in the aza-BODIPYs. The effect of substituents on their photophysical and electrochemical properties was studied; also, computational studies were carried out for the target aza-BODIPYs. These near infrared dyes displayed the lowest energy absorption maxima in the range of 670–738 nm; whereas, their emission maxima were centered on ≈764 nm. The absorption and emission spectra of the aza-BODIPYs were significantly red shifted (72–94 nm) as compared to the parent tetra-phenylaza-BODIPY. Fluorescence studies suggested effective energy transfer (up to 65%) from donor groups to the aza-BODIPY core in all the compounds. TD-DFT studies indicated significant electronic interactions between energy donor groups and the aza-BODIPY core in all the aza-BODIPYs. The values of HOMO–LUMO gap (ΔE) calculated from cyclic voltammetry data were comparable with those obtained from DFT studies.

Graphical abstract: Near infra-red dyes based on pyrene aza-BODIPYs

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The article was received on 08 Sep 2017, accepted on 23 Feb 2018 and first published on 23 Feb 2018

Article type: Paper
DOI: 10.1039/C7NJ03408C
Citation: New J. Chem., 2018,42, 5875-5888
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    Near infra-red dyes based on pyrene aza-BODIPYs

    N. Balsukuri, N. J. Boruah, P. E. Kesavan and I. Gupta, New J. Chem., 2018, 42, 5875
    DOI: 10.1039/C7NJ03408C

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