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Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via Groebke–Blackburn–Bienaymé reaction and studies of optical properties

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Abstract

A series of sixteen new 2-julolidin-imidazo[1,2-a]pyridine bound-type bis-heterocycles were synthesized in good to excellent yields (61–98%) via an MW-assisted Groebke–Blackburn–Bienaymé (GBB) reaction. Then, experimental studies were conducted to determine the luminescence properties of these compounds. Various high quantum yields were found. In fact, one product exhibited a quantum yield (86.6%) comparable to that of the reference compound rhodamine (94.8%). Finally, further computational studies were performed by means of TD-DFT to calculate their HOMO–LUMO distributions and theoretical absorption spectra. A good agreement between the experimental and computational results was obtained, which provides a rationalized explanation for the observed structure/property relationships.

Graphical abstract: Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via Groebke–Blackburn–Bienaymé reaction and studies of optical properties

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Publication details

The article was received on 23 Dec 2016, accepted on 15 Mar 2017 and first published on 16 Mar 2017


Article type: Paper
DOI: 10.1039/C6NJ04044F
Citation: New J. Chem., 2017, Advance Article
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    Synthesis of 2-julolidin-imidazo[1,2-a]pyridines via Groebke–Blackburn–Bienaymé reaction and studies of optical properties

    U. M. V. Basavanag, A. Islas-Jácome, A. Rentería-Gómez, A. S. Conejo, M. Kurva, J. O. C. Jiménez-Halla, J. Velusamy, G. Ramos-Ortíz and R. Gámez-Montaño, New J. Chem., 2017, Advance Article , DOI: 10.1039/C6NJ04044F

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