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Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

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Abstract

The modified Debus–Radziszewski reaction was used to design and synthesize novel truxene derived blue-emitting materials bearing phenanthroimidazole substituents. The materials were prepared non-catalytically under ambient conditions using a triamino based derivative of truxene as a key precursor in good yields. The 5, 5′, 10, 10′, 15, and 15′ positions of the truxene were alkylated to provide solubility to the molecules, making the materials solution processable. The substituted phenanthroimidazole moieties were introduced at the 2, 7, 12 positions of truxene to synthesize the target molecules. Three new materials were prepared by varying the phenyl group attached at the C2 position of the phenanthroimidazole moiety, designated as PT1 for the phenyl, PT2 for the 4-methoxyphenyl, and PT3 for the 4-cyanophenyl substituent. From the photophysical studies, PT3 was found to have dominant charge transfer characteristics in its excited state. Also, PT3 exhibited a photoluminescence quantum yield as high as 0.83. The optimized geometries from the computational studies revealed that the molecules are highly twisted, with dihedral angles of ∼75°. The HOMO–LUMO distributions were found to be well separated showing the bipolar characteristic of the compounds. The band gap values from computational studies were found to be in agreement with experimental values. The emission spectra in the solid state gave maxima at 402 nm for PT1, 412 nm for PT2, and 450 nm for PT3. The materials were thus found to be emitting in the blue region of the visible spectrum. The TCSPC and TRPL studies were carried out to explore further the excited states of the molecules, wherein radiative pathways were found to be dominant.

Graphical abstract: Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

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Publication details

The article was received on 22 Aug 2018, accepted on 20 Dec 2018 and first published on 21 Dec 2018


Article type: Paper
DOI: 10.1039/C8NJ04293D
Citation: New J. Chem., 2019, Advance Article
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    Design and synthesis of highly twisted phenanthroimidazole substituted blue-emitting truxene based fluorescent chromophores

    B. Kaur, D. Moghe, D. Kabra and J. Jacob, New J. Chem., 2019, Advance Article , DOI: 10.1039/C8NJ04293D

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