New 1,3-diazabicyclo-[3.1.0]hex-3-ene photochromic azo dyes: Synthesis, characterization and spectroscopic studies

Mahmoodi, Nosrat O.; Nadamani, Meysam Pasandideh; Behzadi, Tahereh

doi:10.1016/j.molliq.2013.05.026

Cited by 17 publications

(3 citation statements)

References 34 publications

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“…General Methods: The synthesis of starting materials, R‐Azosal (R = H, NO 2 , and CH 3 ) have been reported previously . The reagents o ‐phenylenediamine, salicylaldehyde and para ‐substituted aniline derivatives were purchased from Alfa Aesar.…”

Section: Methodsmentioning

confidence: 99%

Room Temperature Reversible Z→E Photoisomerization of Azobenzene Appended to Anthraquinone‐Benzimidazole Based Photoswitches with Resolved n→π* Absorption Band

2019

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Light‐triggered substituted azobenzene‐based molecular switches are well known for their potential applications as molecular machines. The Z‐isomer stability affected by heteroaromatic groups, extended aromaticity, different substituents, and varying the solvents based on their polarity. In this regards, five different anthraquinone/imidazole‐based azobenzene derivatives have been synthesized with different electronic push/pull substituents. The detailed study of photoswitching processes with kinetic data was appraised by using UV/Vis and 1H‐NMR spectroscopic techniques. The investigation of light‐induced hydroxyl group conversion to quinone‐hydrazone tautomerization has been observed during the isomerization. Most importantly, intermolecular hydrogen bonding interaction between tautomeric form and a higher polar solvent (DMSO) block the isomerization, but in a less polar solvent (DCM), light‐induced trans ↔ cis isomerization takes place by tautomerization pathway with well‐separated π→π* and n→π* transitions. Further, the detailed mechanistic study of solvent‐assisted light‐induced tautomerization with the role of hydrogen bonding and the following WRITE‐READ‐ERASE‐READ system have been derived by using molecular logic gates.

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Section: Methodsmentioning

confidence: 99%

Room Temperature Reversible Z→E Photoisomerization of Azobenzene Appended to Anthraquinone‐Benzimidazole Based Photoswitches with Resolved n→π* Absorption Band

2019

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“…The most prominent feature of these dyes is containing one or more azo groups (-N = N-) that act as bridges between the two organic dyes and at least one of these groups are aromatic [30][31][32]. Azo dyes are used in a variety of elds, such as dyeing, textile, bers, and high-tech applications such as lasers, liquid crystal displays, electro-optical devices, and inkjet printers [33][34][35]. Azo dyes have high e ciency, performance improvement, and short reaction time in reactions, so these compounds are used in medicinal chemistry [36,37].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of New Azoimino-sulfathiazole and Considering Their Antibacterial, Antioxidant and Cytotoxic Activities

Amouee

Mahmoodi

Nyaki

et al. 2022

Preprint

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Sulfonamides are important compounds that have special applications in pharmacy due to their antibacterial and anti-parasitic properties and are known as sulfa-drugs. One of the most important drugs is sulfathiazole. This drug has many uses in the treatment of diseases. In this research, the hybrid reaction between sulfathiazole and various azo compounds was performed via the imine bond. Here, nine new azoiminosulfathiazoles were synthesized, while compound 5g was designed in such a way that two sulfathiazole units were linked by an azo linker. The structure of the newly synthesized hybrid molecules after separation and purification was examined and confirmed by TLC, M.P, FT-IR, 1H NMR, and 13C NMR, and their cytotoxicity was evaluated via MTT assay. Evaluation of antibacterial and antioxidant and anticancer again (PC-3) human prostate line cells using MTT assay properties also showed acceptable results. Comparing 5g with penicillin as a standard drug with the aura of non-growth of bacteria (31 mm) in the presence of Staphylococcus aureus (27 mm) and in the presence of E.coli bacteria showed that it has the best antibacterial properties. Also, evidence shows that some compounds have more effective antibacterial activity than penicillin.

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“…In the light of the above‐mentioned facts, in continuation to our interest in the development of photochromic compounds, for the first time, we report in this article the synthesis of several novel tetraarylimidazoles 1 a ‐ 1 i (Scheme ), phenanthroimidazole 1 j (Scheme ) and bis‐tetraphenylimidazole 1 k (Scheme ), all containing a 2‐methoxyphenol substituent at position 2 of imidazole ring under microwave irradiation and investigate their photochromic properties as well the effects of substituent groups thereon.…”

Section: Introductionmentioning

confidence: 99%

Photochromic Properties of Novel One‐pot Multicomponent Synthesized Tetraarylimidazoles

et al. 2019

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Acetic acid mediated synthesis of novel tetraarylimidazoles derivatives has been reported via multicomponent reaction of benzil or phenanthrene‐9,10‐dione, NH4OAc, vanillin and aniline derivatives under microwave irradiation. Several novel tetraarylimidazole derivatives, phenanthroimidazole and bis‐tetraphenylimidazole bearing a 2‐methoxyphenol substituent at position 2 of imidazole ring were prepared. The advantages of this method are the one‐pot preparation of compounds, in short reaction times (4‐7 min) and good yields. All synthesized compounds with a 2‐methoxyphenol substituent at position 2 of imidazole ring exhibited good photochromic behavior. The photoisomerization can be performed from ground state to triplet excited state according to TD‐DFT calculation. The results showed that the presence of ortho‐methoxy substituent to hydroxyl substitution has the greatest effect on photochromic properties of target compounds. Furthermore, a pattern was successfully visualized upon UV light irradiation, which suggested that these compounds can be served as a security ink or an anti‐counterfeiting mark for photo printing.

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New 1,3-diazabicyclo-[3.1.0]hex-3-ene photochromic azo dyes: Synthesis, characterization and spectroscopic studies

Cited by 17 publications

References 34 publications

Room Temperature Reversible Z→E Photoisomerization of Azobenzene Appended to Anthraquinone‐Benzimidazole Based Photoswitches with Resolved n→π* Absorption Band

Room Temperature Reversible Z→E Photoisomerization of Azobenzene Appended to Anthraquinone‐Benzimidazole Based Photoswitches with Resolved n→π* Absorption Band

Efficient Synthesis of New Azoimino-sulfathiazole and Considering Their Antibacterial, Antioxidant and Cytotoxic Activities

Photochromic Properties of Novel One‐pot Multicomponent Synthesized Tetraarylimidazoles

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