Molecular Logic with Ferrocene-Rylene Conjugates: A Comparison of Naphthalenediimide, Naphthalimide and Perylenediimide Pourbaix Sensor Designs

• Published in: Inorganica Chimica Acta 2023-01, Vol.544, p.121176, Article 121176
• Main Authors: Grech, Joseph, Spiteri, Jake C., Scerri, Glenn J., Magri, David C.
• Format: Article
• Language: English
• Subjects: ferrocene; molecular logic gate; naphthalenediimide; naphthalimide; perylenediimide; photoinduced electron transfer
• ISSN: 0020-1693; 1873-3255
• DOI: 10.1016/j.ica.2022.121176

[Display omitted] •Molecular logic gates based on photoinduced electron transfer are demonstrated.•Molecules are compared comprising of ferrocene and naphthalenediimide, naphthalimide or perylenediimide.•AND logic gates are fluorescent while PASS 0 logic gates are non-fluorescent. Four molecules designed as Pourbaix sensors with rylene dyes (naphthalenediimide, 4-amino-1,8-naphthalimide, perylenediimide) are compared. Each molecule is constructed modularly according to an electron-donor–spacer–fluorophore–spacer–receptor format based on photoinduced electron transfer (PET). The modules consist of ferrocene as the electron donor, a tertiary alkyl amine as the proton receptor, and a rylene dye as the fluorophore connected by a methylene and ethylene spacer, respectively. The proton and oxidant-induced fluorescent spectral changes of the 4-amino-1,8-naphthalimide models include internal charge transfer (ICT) character. Two of the discussed logic gates switch on emitting fluorescence in the presence of acid (H+) and oxidant (Fe3+) according to two-input AND logic, while two of the logic gates remain off according to two-input PASS 0 logic.