Proof of principle for a molecular 1 : 2 demultiplexer to function as an autonomously switching theranostic device

Abstract

Guided by the digital design concepts, we synthesized a two-module molecular demultiplexer (DEMUX) where the output is switched between emission at near IR, and cytotoxic singlet oxygen, with light at 625 nm as the input (I), and acid as the control (c). In the neutral form, the compound fluoresces brightly under excitation at 625 nm, however, acid addition moves the absorption bands of the two modules in opposite directions, resulting in an effective reversal of excitation energy transfer direction, with a concomitant upsurge of singlet oxygen generation and decrease in emission intensity.

Supramolecular tuning of energy transfer efficiency and direction in a bis(styryl) dye–crown ether conjugate

“…1 H NMR spectra were recorded at 300 or 600 MHz, 13 C NMR spectra were recorded at 150 MHz at ambient temperature using 5 mm tubes. Chemical shifts were determined with accuracy of 0.01 ppm and 0.1 ppm for 1 H and 13 C spectra, respectively, and are given relative to the residual signal of the solvent that was used as internal reference. Spin spin coupling constants for the proton spectra were determined with accuracy of 0.2 Hz.…”

“…For example, such switching has been realized by changing the complexed metal cations in homo and heterodimers of metalloporphyrins [7], metallocyclodextrin assemblies [8] and [2] ca tenates incorporating the [Ru(tpy) 2 ] 2+ fragment [9]. The control of the FRET direction can be also accomplished by protonation/deprotonation of the donor or acceptor unit as has been shown for oligophenylene vinylene (OPV) phenanthroline [10] and OPV fullerene [11] dyads and for multichromophoric BODIPY systems [12,13]. In addition, sev eral intriguing examples of switchable FRET directions have been re ported that use site specific solvent effects [14], temperature changes [15] or the electronic difference between cation binding sites [16,17].…”

Selected applications of calixarene derivatives

“…Today photodynamic therapy (PDT) 62 has been developed as a less invasive alternative to traditional therapeutic methods such as surgery or chemotherapy. In PDT procedure the light, singlet oxygen and a photosensitizer are necessary, therefore recently many reports concern the search for new photosensitizers.…”

Strongly Emissive and Photostable Four‐Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

“…[1][2][3][4] The structural scope includes N,O-and N,Nchelates with five-and six-membered rings as most common binding motifs [3,5] as well as bi-nuclear boron complexes. [6] Prominent examples are boron 8-hydroxyquinolinate complexes, [7,8] boron dipyrromethene (Bodipy) dyes, [9][10][11] boranils, [12,13] and boron iminocoumarins (Boricos).…”