New Labels and Probes for the Application in Bionanophotonics

5′-Substituted Indoline Spiropyrans: Synthesis and Applications

“…in a number of reviews and monographs [21][22][23]25], and they have been supplemented by more recent results from our lab at IBCP as well as other research groups [4,[9][10][11]16,24,26].…”

“…For the series of substituted dyads (SP263-SP265, SP270, SP271, SP273) containing a fragment of the stilbene fluorophore at the 5 -position of the indoline part of the photochromic molecule, the nature of the substituents in the aryl ring of the fluorophore was found to have the strongest influence mainly on the spectra of the spiroform (A): λ A max 335-409 nm (∆λ A max 74 nm) in ethanol and λ A max 325-407 nm (∆λ A max 82 nm) in toluene solutions. The difference in the λ max for the Zand E-isomers in the series of these derivatives, containing a substituted aryl ring in the stilbene fluorophore fragment for spiroform (A) was small (∆λ A max 7-9 nm) and it was almost absent for the MC form [16,50].…”

“…At present, significant progress has been made in synthesis and study of the polyfunctional properties of photochromic organic compounds of the following classes of spiropyrans, spirooxazines, chromenes, diarylethylenes, fulgides, indigoids, etc. [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. Since the discovery of the spiropyran photochromism in the 1950s by Hirshberg [20] and in the course of more than 70 years of subsequent development, the photoactive materials with photoswitchable fragments have found their applications in various scientific research fields, ranging from chemistry, physics, and materials science, to biology and nanotechnology, but not in industry.…”

“…The most promising approach toward design and development of these hybrid photoactive and photo-controlled systems and materials consists of binding the photochromic labels by covalent immobilization onto the surface or into the active binding site of the targets, e.g., various substrates, polymers, DNA, lipids, proteins, cations, and quantum dots. To perform this procedure, it is necessary to develop a new generation of photochromic labels and probes containing substituents with the respective types of functional groups [16].…”

“…The results of comprehensive investigation of the structure and characteristics of 5substituted spiropyrans largely up to year 2000 already have been discussed and analyzed in a number of reviews and monographs [21][22][23]25], and they have been supplemented by more recent results from our lab at IBCP as well as other research groups [4,[9][10][11]16,24,26].…”