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Issue 18, 2017
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Perylene diimide-based organic π-motif for differentiating CN and F ions by electron-transfer and desilylation mechanisms: applications to complex logic circuits

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Abstract

In this work, we have designed and synthesized a perylene diimide based derivative PDI-SiHQ having an O-silylated-8-hydroxyquinoline group at the bay position. PDI-SiHQ is able to detect and differentiate CN from F in the presence of other anions. The electron transfer from cyanide ions to PDI-SiHQ leads to the emergence of panchromatic and NIR absorption bands due to the formation of a PDI-SiHQ˙ radical anion. In contrast, fluoride induced desilylation of PDI-SiHQ coupled with π–π aggregation results in a red-shifted absorption band at 730 nm. 1H NMR and cyclic voltammetry combined with the reversal of the PDI-SiHQ˙ radical anion to the PDI-SiHQ neutral form in the presence of NOBF4 or Cu2+ ions confirm the formation of the radical anion in PDI-SiHQ. Multi-channel UV-Vis-NIR absorption and emission bands and their reversibility with NOBF4/Cu2+ ions offer the possibility for fabrication of complex logic circuits such as complementary IMP/INH logic circuits, magnitude comparators and ‘set–reset’ flip flop memory elements.

Graphical abstract: Perylene diimide-based organic π-motif for differentiating CN− and F− ions by electron-transfer and desilylation mechanisms: applications to complex logic circuits

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Publication details

The article was received on 03 Jul 2017, accepted on 10 Aug 2017 and first published on 10 Aug 2017


Article type: Paper
DOI: 10.1039/C7NJ02380D
Citation: New J. Chem., 2017,41, 10281-10290
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    Perylene diimide-based organic π-motif for differentiating CN and F ions by electron-transfer and desilylation mechanisms: applications to complex logic circuits

    P. Singh, L. S. Mittal, H. Singh, G. Bhargava and S. Kumar, New J. Chem., 2017, 41, 10281
    DOI: 10.1039/C7NJ02380D

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