Synthesis, chemosensing properties and logic behaviour of a novel ratiometric 1,8-naphthalimide probe based on ICT and PET

• Published in: Dyes and pigments 2016-08, Vol.131, p.9-17
• Main Authors: Georgiev, Nikolai I., Dimitrova, Margarita D., Todorova, Yoana D., Bojinov, Vladimir B.
• Format: Article
• Language: English
• Subjects: 1,8-Naphthalimide; Combinatorial analysis; Comparators; Digital; Disabled-INHIBIT and disabled-IMPLICATION logic gates; Dyes; Fluorescence; Internal charge transfer (ICT); Logic circuits; Photoinduced electron transfer (PET); Ratiometric fluorescence probe; Signalling; Synthesis; Three input disabled-XNOR; Two output combinatorial logic circuit
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2016.03.051

A novel fluorescence sensing 1,8-naphthalimide designed on the “receptor1-fluorophore-spacer-receptor2” model is synthesized and investigated. The novel probe comprising aminotriazole and hydroxyphenyl substituents is capable to operate simultaneously via ratiometric ICT and PET signalling mechanism. The synthesized compound shows excellent signalling properties towards protons, hydroxyl anions and Cu2+ ions. Due to the remarkable fluorescence changes in the presence of these analytes the system is able to act as a two output combinatorial logic circuit with three chemical inputs. Input3-Disabled XNOR, INHIBIT and IMPLICATION logic gates were obtained. Because of the parallel action of disabled-XNOR and disabled-INHIBIT gates a magnitude digital comparator with disable capability is achievable. [Display omitted] •Ratiometric 1,8-naphthalimide probe based on ICT and PET is synthesized.•System manifests excellent signalling response to protons, hydroxide and Cu2+ ions.•Input3-Disabled XNOR, INHIBIT and IMPLICATION logic gates are executed.•Two output combinatorial logic circuit with three chemical inputs is demonstrated.•A magnitude digital comparator with disable capability is achievable.