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2-[(E)-2-phenylvinyl]-3-methyl-1,3-benzothiazol-3-ium iodide is a cationic stilbene derivative belonging to the class of benzothiazolium-based photoswitches. It exhibits hypsochromic-shifted absorption and bathochromic-shifted fluorescence spectra due to its larger dipole moment in the excited state compared to the ground state. 2-[(E)-2-phenylvinyl]-3-methyl-1,3-benzothiazol-3-ium iodide undergoes fast photoisomerization upon UV or visible light irradiation, forming a Z-isomer with a distinct blue-shifted absorption maximum, which thermally reverts to the E-isomer more rapidly than conventional stilbenes. Its photochromic properties, including high Z-isomer content in the photostationary state and solvent-dependent thermal isomerization kinetics, make it a potential candidate for optical data storage applications. The phenyl-substituted derivative shows faster thermal relaxation compared to larger aryl-ring analogues.

118357-46-3

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118357-46-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 118357-46-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,3,5 and 7 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 118357-46:
(8*1)+(7*1)+(6*8)+(5*3)+(4*5)+(3*7)+(2*4)+(1*6)=133
133 % 10 = 3
So 118357-46-3 is a valid CAS Registry Number.

118357-46-3Relevant academic research and scientific papers

Photophysics, photochemistry and thermal stability of diarylethene-containing benzothiazolium species

El-Hendawy, Morad M.,Fayed, Tarek A.,Awad, Mohamed K.,English, Niall J.,Etaiw, Safaa Eldin H.,Zaki, Ahmed B.

, p. 20 - 31 (2015)

The photophysics, photochemistry and thermal stability of four 1-aryl-2-(N-methyl-2-benzothiazolium) ethene iodides (aryl: phenyl, 1-naphthyl, 9-phenanthryl and 9-anthryl) were studied. Although the absorption spectra are found to be hypsochromic-shifted, fluorescence spectra are bathochromic-shifted. The dipole moment in the relaxed excited state was found to be larger than that in the ground state. To investigate effects of N-methylation and the aryl-ring size, a detailed comparison was made between those in the present work (of charged compounds) and previous studies of their neutral analogues, with computed electron affinity and ionisation potentials serving to rationalise the experimentally observed bathochromic shifts in absorption and emission spectra. The kinetics of thermal isomerisation depend strongly on the nature of the aryl moiety and solvent; the larger the aryl ring, the slower the rate of isomerisation. The fastest isomerisation process was found to take place in MeOH. The anthryl derivative did not isomerize either by light- or heat-exposure, due to high energy barriers of rotation around the ethenic bond. Based on the significant blue-shift of the Z-isomer absorption maximum relative to that of the E-isomer, and the high percentage of Z-isomers in the photostationary state, these compounds may serve as potential promising candidates for optical data-storage applications.

Fast (hetero)aryl-benzothiazolium ethenes photoswitches activated by visible-light at room temperature

Coelho, Paulo J.,Castro, M. Cidália R.,Raposo, M. Manuela M.

, p. 163 - 169 (2015)

A series of novel photochromic cationic stilbenes dyes bearing different aromatic systems were easily synthesized from (hetero)aromatic aldehydes. The photoisomerization of the double bond can be achieved through irradiation with ultraviolet or visible light, for few seconds, leading to the Z isomers that return much faster to the initial state than common stilbenes. Benzothiazolium dyes with electron donating substituents exhibited very fast thermal back reactions (1 s). Pyrrole-benzothiazolium dye showed a higher lifetime of the Z isomer, in different solvents, including water (0.45-7.1 min). This cationic diarylethene can be switched between the E-Z states using visible light, in few minutes at room temperature, with a noticeable change in the visible spectrum.

Design and Synthesis of Novel c-di-GMP G-Quadruplex Inducers as Bacterial Biofilm Inhibitors

Chen, Wei-Min,Lin, Jing,Lin, Qian-Wen,Liu, Jun,Wang, Zi-Qiang,Xuan, Teng-Fei,Yu, Hai-Tao

, p. 11074 - 11089 (2021/08/20)

The formation of biofilms by clinical pathogens typically leads to chronic and recurring antibiotic-resistant infections. High cellular levels of cyclic diguanylate (c-di-GMP), a ubiquitous secondary messenger of bacteria, have been proven to be associate

Benzothiazole compounds and application thereof in preparation of bacterial biofilm inhibitors

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Paragraph 0064-0066; 0085-0087, (2019/07/04)

The invention belongs to the medical field and discloses benzothiazole compounds as well as a preparation method and an application thereof. The benzothiazole compounds have the structural formula shown in formula I, wherein Ar is substituted benzene ring

Synthesis and study of novel benzothiazole derivatives with potential nonlinear optical properties

Sigmundova, Ivica,Zahradnik, Pavol,Loos, Dusan

, p. 1069 - 1093 (2008/12/22)

The synthesis of new benzothiazole push-pull systems as candidates for NLO-phores is described. Spectral (UV/VIS and solvatochromic) and theoretical studies (electronic properties based on semiempirical AM1 and PM3 methods) of the prepared compounds were carried out. The structure and physico-chemical parameters affecting the push-pull character and intramolecular charge transfer (ICT) of the studied compounds have been investigated and compounds with enhanced hyperpolarizability β have been predicted. The benzothiazolium salts were found to be much more effective NLO-phores in comparison with the corresponding neutral benzothiazoles. The 4-NPh2 group is the most effective donor. The extension of conjugated bridge improves the studied NLO characteristics. An additional acceptor group bonded to the heterocycle causes a red shift of λmax but does not increase hyperpolarizability.

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