Reversibly Photo-Switchable Nucleosides: Synthesis and Photochromic Properties of Diarylethene-Functionalized 7-Deazaadenosine Derivatives was written by Singer, Marco;Jaeschke, Andres. And the article was included in Journal of the American Chemical Society in 2010.Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:
Photochromic nucleosides, e.g. I, were designed that combine the structural features and mol. recognition properties of nucleic acids with the light-sensitivity of diaryl-ethenes. Target compounds, e.g. I, consist of a 7-deazaadenosine unit that is linked to a thiophene as the second aryl functionality via a 1,2-cyclopentenyl linker. These nucleoside analogs undergo a reversible electro-cyclic rearrangement, generating strongly colored closed-ring isomers upon irradiation with UV-light, while exposure to light in the visible range triggers the cyclo-reversion to the colorless opened-ring form. UV-vis spectroscopy, HPLC, and 1H NMR measurements revealed recognition of complementary thymidine and up to 97% conversion to the thermally stable closed-ring isomers after illumination with UV-light. The required wavelength for ring closure was found to vary depending on the substituents attached to the thiophene moiety. In a first design step, we used this important feature of diaryl-ethenes, e.g. I, to shift the switching wavelength from initially 300 nm to 405 nm. In a second step, we generated a pair of orthogonal switches, differing enough in their resp. switching wavelengths to be controlled independently in the same sample. Finally, a mol. switch was developed that showed both photochromism and acidichromism, thereby illustrating the possibility to gate the spectral properties to multiple stimuli. These new photochromic nucleosides represent useful building blocks for the generation of light-sensitive nucleic acids either by inducing conformational changes upon isomerization or by exploring the different spectral properties of the closed and opened isomers, for example, for use as reversible fluorescence quenchers. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene).
3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. It is also used in the manufacturing of dyes such as thioindigo.Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem