Synthesis,Structure, and Optical Studies of Donor–Acceptor‐Type Near‐Infrared (NIR) Aza–Boron‐Dipyrromethene (BODIPY) Dyes |
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Authors: | Naresh Balsukuri Mohsin Y. Lone Dr. Prakash C. Jha Dr. Shigeki Mori Dr. Iti Gupta |
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Affiliation: | 1. Indian Institute of Technology Gandhinagar, Village Palaj, Simkheda, Gandhinagar, Gujarat-, India;2. School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat, India;3. Integrated Centre for Sciences, Ehime University, Matsuyama, Japan |
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Abstract: | Six donor–acceptor‐type near‐infrared (NIR) aza–boron‐dipyrromethene (BODIPY) dyes and their corresponding aza–dipyrrins were designed and synthesized. The donor moieties at the 1,7‐positions of the aza–BODIPY core were varied from naphthyl to N‐phenylcarbazole to N‐butylcarbazole. The 3,5‐positions were also substituted with phenyl or thienyl groups in the aza–BODIPYs. Photophysical, electrochemical, and computational studies were carried out. The absorption and emission spectra of aza–BODIPYs were significantly redshifted (≈100 nm) relative to the parent tetraphenylaza–BODIPY. Fluorescence studies suggested effective energy transfer (up to 93 %) from donor groups to the aza–BODIPY core in all of the compounds under study. Time‐dependent (TD)‐DFT studies indicated effective electronic interactions between energy donor groups and aza–dipyrrin unit in all the aza–BODIPYs studied. The HOMO–LUMO gap (ΔE) calculated from cyclic voltammetry data was found to be lower for six aza–BODIPYs relative to their corresponding aza–dipyrrins. |
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Keywords: | density functional calculations donor– acceptor systems dyes/pigments energy transfer X-ray diffraction |
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