55526-95-9Relevant academic research and scientific papers
Crown ether styryl dyes 18. Synthesis, anion-"capped" complexes, and ion-selective stereospecific [2+2] autophotocycloaddition of photochromic 18-crown-6 ethers
Gromov,Ushakov,Fedorova,Buevich,Alfimov
, p. 654 - 661 (1996)
New crown ether styryl dyes (trans- 1c,d) containing the 18-crown-6 ether fragment were synthesized. Interaction of trans-1c,d dyes, as well as their analogs, trans-1a,b containing the 15-crown-5 ether fragment, with Ca(ClO4)2 in MeCN afforded supramolecular structures (dimeric complexes). Competing reactions, trans-cis-photoisomerization with the formation of anion-"capped" complexes of cis-1a-d and [2+2] autophotocycloaddition with the formation of cyclobutane derivatives 8a-d and 9c, were observed on photolysis of solutions of complexes of trans-1a-d with Ca2+. Preorganization of trans-isomers in dimeric complexes with Ca2+ determined the regio- and stereoselectivity of each of the two directions of the photocycloaddition and the efficiency of the reaction.
Novel synthetic route to pH-sensitive 2,6-bis(substituted ethylidene)cyclohexanone/hydroxycyanine dyes that absorb in the visible/near-infrared regions
Strekowski, Lucjan,Mason, J. Christian,Say, Martial,Lee, Hyeran,Gupta, Rajni,Hojjat, Maryam
, p. 129 - 134 (2005)
Succinimide N-oxide anion-mediated reaction of heptamethine cyanines that are chloro substituted at the central position of the heptamethine moiety furnishes the title dyes in high yield (80-96%). The ketones absorb in the visible region, and upon protona
Highly selective turn-on red fluorescence probes for visualization of the G-quadruplexes DNA in living cells
Kang, Yongqiang,Wei, Chunying
, (2021/10/27)
Studies on small molecule fluorescent probes for detecting G-quadruplexes DNA have bring about an extensive attention in recent years. In this paper, we designed and synthesized three benzothiazole derivatives named 2a-2c under moderate reaction conditions and investigated their interactions with DNA (single-stranded, duplex, i-motif and G-quadruplex) and distribution in living cell. Three compounds present a large Stokes shift (～90 nm) and a weak red fluorescence emission, and they exhibit a good selectivity and sensitive turn-on fluorescence response for the promoter G-quadruplex DNA (bcl-2, c-myc and c-kit 2) and mitochondria G-quadruplex (KSS). The affinity of 2a and 2b with N-alkyl side chain group to DNA is stronger than that of 2c with an anion group, therefore, they also increase the stability of the G-quadruplex structure. 2b induces the conformational change of both bcl-2 and KSS G-quadruplexes, while all compounds induce the folding of bcl-2 from the coiled structure to the hybrid G-qrudruplex. Three compounds interact with the G-quadruplex DNA mainly by end-stacking mode. Furthermore, MTT assays and confocal fluorescence images show that these compounds can enter the living HepG2 cells with low cytotoxicity. 2a-2c are mainly located in the mitochondrion and interacted with mitochondria G-quadruplex DNA, while only weak fluorescence can be found in cell nucleus. In a word, 2a-2c can be implied in image of G-quadruplex DNA in living cells.
Accumulation of the photonic energy of the deep-red part of the terrestrial sun irradiation by rare-earth metal-free: E - Z photoisomerization
Baluschev, Stanislav,Dimitrova, Ralitza,Kandinska, Meglena,Landfester, Katharina,Vasilev, Aleksey
, p. 7119 - 7126 (2021/06/16)
Large scale solar energy storage in the form of E-Z photoisomerisable organic materials requires avoidance of applying rare earth metals at any stage of the process used. Here, drastic shortening of the synthetic route of crown ether functionalized hemicyanine dyes, suitable for efficient E-Z photoisomerization under extremely low excitation light intensities compared with unconcentrated sunlight is reported. The higher energetic form was successfully stabilized by rare earth free cations-in this case by styryl dye-Ba2+ complexes. For the first time E-Z photoisomerization was demonstrated and was observed directly by excitation with light substantially red-shifted compared to the absorption spectrum of the trans-to-cis active moieties via the process of triplet-triplet annihilation upconversion.
Novel hemicyanine sensitizers based on benzothiazole-indole for dye-sensitized solar cells: Synthesis, optoelectrical characterization and efficiency of solar cell
Al-Ostoot, Fares H.,Al-horaibi, Sultan A.,Alghamdi, Mohammed T.,Alrabie, Ali A.,Garoon, Eman M.,Rajbhoj, Anjali S.
, (2020/08/11)
Synthesis, characterization, and photovoltaic properties of three new hemicyanine sensitizers based benzothiazole-indoline (HC-TH, HC-IND1 and HC-IND2) were tested in DSSC with TiO2 film. These sensitizers have a higher molar absorption coefficient, and thus have better light harvesting properties. Electrochemical, theoretical, and spectroscopic methods were used to calculate energy levels of the dye molecules both in the excited state and in the ground state. The results obtained from the spectroscopy and Tafel studies show a marked increase in overall photoelectro-chemical cell output with Br-substitute at p-position in the hemicyanine sensitizer. Interestingly, HC-IND2 showed absorption of UV–Vis at a longer wavelength than HC-IND1 and HC-TH. This structural feature, as well as optical properties, would result in an improved efficiency of DSSC with a better photovoltaic output (4.01percent) solar to electricity conversion efficiency compared to HC-IND1 and HC-TH.
N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections
Critchley, Megan E.,Lawrence, Clare L.,McKenna, Sean T.,Okoh, Adeyi Okoh,Smith, Robert B.,Vishwapathi, Vinod
supporting information, (2020/07/21)
In this study, eighteen heptamethine dyes were synthesised and their antifungal activities were evaluated against three clinically relevant yeast species. The eighteen dyes were placed within classes based on their core subunit i.e. 2,3,3-trimethylindolenine (5a-f), 1,1,2-trimethyl-1H-benzo[e]indole (6a-f), or 2-methylbenzothiazole (7a-f). The results presented herein imply that the three families of cyanine dyes, in particular compounds 5a-f, show high potential as selective scaffolds to treat C. albicans infections. This opens up the opportunity for further optimisation and investigation of this class compounds for potential antifungal treatment.
Indoline and benzothiazole-based squaraine dye-sensitized solar cells containing bis-pendent sulfonate groups: Synthesis, characterization and solar cell performance
Al-horaibi, Sultan A.,Asiri, Abdullah M.,El-Shishtawy, Reda M.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
, p. 591 - 597 (2019/06/18)
Two new symmetric squaraine sensitizers (SQTHZ and SQIND) carrying benzothiazole and indoline moieties as strong electron donating groups to inject the electron into the TiO2 nanoparticles were tested as DSSC. The theoretical calculations and absorption results show that the electron density of LUMO of SQTHZ is delocalized in the whole chromophore, leading to strong electronic coupling between SQTHZ sensitizer and the conduction band of TiO2. Furthermore, the presence of long alkyl chain with pendent bis-SO3 - groups would inhibit recombination and decrease the dye aggregation. Interestingly, SQTHZ displayed UV–Vis and NIR absorption at a longer wavelength compared to SQIND. This structure feature, as well as optical properties, would lead to improved efficiency of dye-sensitized solar cell with overall better photovoltaic performance (η of 3.31%, Jsc of 7.65 mA/cm2, Voc of 0.59, ff of 0.71 and IPCE of 47% at 674 nm) compared to SQIND.
Precious metal-free molecular machines for solar thermal energy storage
Kandinska, Meglena I.,Kitova, Snejana M.,Videva, Vladimira S.,Stoyanov, Stanimir S.,Yordanova, Stanislava B.,Baluschev, Stanislav B.,Angelova, Silvia E.,Vasilev, Aleksey A.
supporting information, p. 1096 - 1106 (2019/06/08)
Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes (4b and 4d) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of trans-cis photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV-vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability constants of metal complexes were determined and are in good agreement with the literature data for reference dyes. The temporal evolution of trans-to-cis isomerization was observed in a real-time regime. The dyes demonstrated a low intrinsic fluorescence of their Ba2+ complexes and high yield of E/Z photoisomerization with lifetimes of the higher energy form longer than 500 seconds. Density functional theory (DFT) calculations at the B3LYP/6-31+G(d,p) level were performed in order to predict the enthalpies (H) of the cis and trans isomers and the storage energies (ΔH) for the systems studied.
Promising near-infrared non-targeted probes: Benzothiazole heptamethine cyanine dyes
Okoh, Okoh Adeyi,Bisby, Roger H.,Lawrence, Clare L.,Rolph, Carole E.,Smith, Robert B.
, p. 42 - 56 (2014/01/06)
A series of benzothiazole heptamethine cyanine dyes have been synthesized and their photophysical properties evaluated in relation to their structural features. These have been compared against two classical probes of this type: Indocyanine Green (IGC) and New Indocyanine Green (IR-820). Growth inhibitory studies were also performed using a eukaryotic, unicellular organism, fission yeast Schizosaccharomyces pombe. Herein we highlight some potentially interesting candidates with improved fluorescence quantum yields when compared with ICG and IR-820.
Highly selective and sensitive colourimetric detection of Hg2+ ions by unsymmetrical squaraine dyes
Shafeekh,Rahim,Basheer,Suresh,Das
, p. 714 - 721 (2013/03/14)
A novel class of sulphonate group containing unsymmetrical squaraine dyes has been synthesized. These dyes show a selective and sensitive affinity towards Hg2+ in methanol and are practically insensitive to most other environmentally and biologically relevant metal ions. Isothermal titration calorimetric (ITC) studies and High Resolution Mass Spectral (HRMS) analysis indicate a 1:1 binding mode. 1H and 13C NMR of the isolated Dye...Hg2+ adduct showed an unusual addition reaction of Hg2+ along the phenyl-squarate carbon-carbon bond which was also supported by TD-DFT calculations using PM6 level geometries.
