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Perylene diimide-based organic π-motif for differentiating CN- and F- ions by encounter of electron-transfer vs. desilylation mechanisms: Applications to complex logic circuits

Abstract

In this work, we have designed and synthesized perylene diimide based derivative PDI-SiHQ having O-silylated-8-hydroxyquinoline group at 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 emergence of panchromatic and NIR absorption bands due to formation of PDI-SiHQ˙− radical anion. In contrary, fluoride induced desilylation of PDI-SiHQ coupled with π-π aggregation results in red-shifted absorption band at 730 nm. The 1H NMR and cyclic voltammetry combined with reversal of PDI-SiHQ˙− radical anion to PDI-SiHQ neutral form in the presence of NOBF4 or Cu2+ ions confirm the formation of radical anion in PDI-SiHQ. The 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 comparator and ‘set- reset’ flip flop memory elements.

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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, Accepted Manuscript
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    Perylene diimide-based organic π-motif for differentiating CN- and F- ions by encounter of electron-transfer vs. desilylation mechanisms: Applications to complex logic circuits

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

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