Cyclic naphthalene diimides (cNDIs), with a ferrocene moiety (cFNDs) and different linker lengths between the ferrocene and cNDI moieties, were designed and synthesized as redox‐active, tetraplex‐DNA ligands. Intramolecular stacking was observed between ferrocene and the NDI planes, which could affect the binding properties for G‐quadruplexes. Interestingly, the circular dichroism spectrum of one of these compounds clearly shows new Cotton effects around 320–380 and 240 nm, which can be considered a direct evidence of intramolecular stacking of ferrocene and the NDI. Regarding recognition of hybrid G‐quadruplexes, the less rigid structures (longer linkers) show higher binding affinity (106 m−1 order of magnitude). All new compounds show higher selectivity for G4 during electrochemical detection than noncyclic FND derivatives, which further identifies the redox‐active potentiality of the cFNDs. Two of the three compounds tested even show preferential inhibition of cell growth in cancer cells over normal cells in a low concentration range, highlighting the potential for bioapplications of these cFNDs.

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Newly synthesized naphthalene diimide carrying two β-cyclodextrins (NDI-β-CyDs) showed improved specificity for the parallel G-quadruplex structure alongside the hybrid G-quadruplex structure. Specifically, the highest binding affinity of NDI-β-CyDs for the telomere RNA G-quadruplex was observed. The binding simulation indicated that β-cyclodextrins might be available for loop nucleobase inclusion under its complex.

To develop an electrochemical detection method for COVID-19, we have investigated the interaction between RG-1, a characteristic parallel four-strand RNA component of the COVID-19 genome, and cyclic ferrocenylnaphthalene diimides carrying different linker lengths 1 and 2, which bind to RG-1 more strongly than cyclic naphthalene diimide 3 that lacks a ferrocene moiety. In particular, the binding affinity of 1 having short one showed the highest binding affinity to RG-1, and the redox current of 1 increased in the presence of RG-1 using a glassy carbon electrode. This increasing current of 1 in the presence of c-myc as a parallel G4 DNA or single-stranded RNA was lower than that in the presence of RG-1. Several RG-1 was electrochemically detected at the nanomolar level by 1.

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