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Near Infra-Red Dyes Based on Pyrene Aza-BODIPYs


Pyrene substituted donor-acceptor type NIR aza-BODIPYs were designed and synthesized. The 1,7-positions of aza-BODIPY core were substituted by pyrene moieties and 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 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 aza-BODIPY core in all the aza-BODIPYs. The values of HOMO-LUMO gap (E) calculated from cyclic voltammetry data were comparable with those obtained from DFT studies.

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Publication details

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, Accepted Manuscript
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    Near Infra-Red Dyes Based on Pyrene Aza-BODIPYs

    I. -. GUPTA, N. Balsukuri, P. E. Kesavan and N. J. Boruah, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7NJ03408C

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