A fluorescent combinatorial logic gate with Na+, H+-enabled OR and H+-driven low-medium-high ternary logic functions12. Issue 47 (24th November 2017)

• Record Type: Journal Article
• Authors: Spiteri, Jasmine M. A.; Mallia, Carl J.; Scerri, Glenn J.; Magri, David C.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 47(2017)
• Page Start: 10116
• Page End: 10121
• Publication Date: 2017-11-24
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob01828b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A fluorescent combinatorial Na +, H + logic gate is demonstrated that could represent a class of probes for investigating antiporters in biological systems. Abstract : A novel fluorescent molecular logic gate with a ' fluorophore – spacer 1 – receptor 1 – spacer 2 – receptor 2 ' format is demonstrated in 1 : 1 (v/v) methanol/water. The molecule consists of an anthracene fluorophore, and tertiary alkyl amine and N -(2-methoxyphenyl)aza-15-crown-5 ether receptors. In the presence of threshold concentrations of H + and Na +, the molecule switches 'on' as an AND logic gate with a fluorescence quantum yield of 0.21 with proton and sodium binding constants of log β H+ = 9.0 and log β Na+ = 3.2, respectively. At higher proton levels, protonation also occurs at the anilinic nitrogen atom ether with a log β H+ = 4.2, which allows for Na +, H + -enabled OR (OR + AND circuit) and H + -driven ternary logic functions. The reported molecule is compared and contrasted to classic anthracene-based Na + and H + logic gates. We propose that such logic-based molecules could be useful tools for probing the vicinity of Na +, H + antiporters in biological systems.