66749-96-0Relevant academic research and scientific papers
A new colorimetric and fluorescent chemosensor based on Schiff base-phenyl-crown ether for selective detection of Al3+ and Fe3+
Dong, Guangcui,Duan, Kaifei,Zhang, Qiang,Liu, Zizhong
, p. 322 - 330 (2019)
A novel chemosensor (L) based on Schiff base-phenyl-crown ether was synthesized and evaluated as a chemoselective Al3+ and Fe3+ sensor in ethanol through “turn-on” fluorescence enhancement and sharp colorimetric responses. Adding 10 equiv. Al3+ or Fe3+ could change the color of the sensor L from colorless to orange yellow, and increase the fluorescence intensity of L at 596 nm by 160-fold or 130-fold, respectively. The selective response of L to Al3+ and Fe3+ was not interfered by other ions, and their bonding was reversible. The results of fluorescence spectral titration data showed that the association constants (lgKs) of L for Al3+ and Fe3+ were 8.95 and 8.67 in ethanol, and the corresponding detection limits were 0.33 and 0.36 μM, respectively. The Job's plot and mass spectrometry revealed that the sensor L formed a 2:1 complex with Al3+ or Fe3+. The proposed binding modes of L with Al3+ and Fe3+ were demonstrated by means of the infrared spectroscopy and 1H NMR titration. The results of DFT/B3LYP calculations showed that the binding with Al3+ and Fe3+ makes the sensor L accompanied a mechanism with the inhibition of C[dbnd]N isomerization (cis-trans) and the activation of chelation enhanced fluorescence (CHEF).
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.
A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+
Zhang, Qiang,Ma, Ruifang,Li, Zhuying,Liu, Zizhong
, (2019/12/09)
A novel multi-response chemosensor L based on coumarin-chalcone-crown ether was designed and synthesized, which exhibited a high selectivity for the colorimetric detecting Al3+ and Cu2+ and fluorescent recognizing Al3+ and Mg2+ in ethanol. L can monitor Al3+ and Cu2+ via distinct color changes from a slight yellow to pink and to orange, respectively. The sensor L can also monitor Al3+ and Mg2+ by fluorescence emission responses at 592 nm and 547 nm with low detection limits of 0.31 μM and 0.23 μM, respectively. The selectivity of L toward Al3+, Cu2+ and Mg2+ was not interfered by a large number of coexisting ions and was found to be reversible. By means of spectrometric titration, Job's plot, mass spectrometry, 1H NMR titration and IR spectroscopy analysis, it was unanimously confirmed that the sensor L had a stoichiometric ratio of 1:1 with Cu2+ and Mg2+, and 1:2 with Al3+. The order of the stability of the complexes formed by L and Al3+, Cu2+, Mg2+ was as follows: L-Al3+ > L-Cu2+ > L-Mg2+. At the same time, some possible bonding modes and sensing mechanisms were further proposed, and the optimized structure of the sensor L and its sensing mechanism for Al3+, Cu2+ and Mg2+ were confirmed by the calculations of DFT/B3LYP and TD-DFT methods in a suite of Gaussian 09 programs.
Synthesis and Characterization of Two Novel Oxazol-5-ones Derivatives and Their Multifunctional Properties; pH Sensitivity, Electropolymerizability and Antiproliferative Activity
Nazl?, ?brahim Hanif,Alp, Serap,Topkaya, Derya,Güney Afacan, ?mran,Nalbantsoy, Ay?e
, p. 1063 - 1073 (2020/07/10)
The aim of this study is to synthesize oxazol-5-one derivatives, which have multi-functional properties. Nomenclatures of newly synthesized molecules are 4-(4-N,N-diethylaminophenylmethylene)-2-(3-thienyl)oxazol-5-one (4a) and 4-(4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)phenylmethylene)-2-(3-thienyl)oxazol-5-one (4b). These two novel derivatives contain pH sensitive and polymerizable groups. 3-Thienyl group was attached to position-2 of the oxazol-5-one ring to provide electrochemical polymerization capability. pH sensing properties were provided by attaching p-N,N-diethylaminophenylmethylene and p-aza-15-crown-5-phenylmethylene groups to the arylmethylene moiety at position-4 of the ring. Target molecules were synthesized by classical process known as Erlenmeyer-Pl?chl Azlactone Synthesis Erlenmeyer (Justus Liebigs Ann Chem 275:1-12, 1893), Rodrigues et al. (J Chem Educ 92:1543-1546, 2015). After structural characterization of 4a and 4b, absorption and emission characteristics were determined in solvents that have different polarities. Difference in maximum absorption and emission wavelengths of the molecules related to solvent polarities were observed at around 6–7 nm and 35–36 nm respectively. In pH studies of the target derivatives in PVC polymer matrix, ratiometric changes were observed at isosbestic point around 398 nm. Polymeric depositions of the molecules (4a, 4b) were proved by using cyclic voltammetry, electrochemical impedance spectrometry studies and scanning electron microscope images. MTT assay studies showed significant results like, 4b derivative’s strong cytotoxic activity on PC-3 (cancerous cell line) with IC50 value of 12.57 ± 0.41 μg/ml without exhibiting any cytotoxic effect on HEK293 (healthy cell line).
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.
, 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.
Fluorescence chemosensor containing 4-methyl-7-coumarinyloxy, acetylhydrazono and N-phenylaza-15-crown-5 moieties for K+ and Ba2+ ions
Zhang, Qiang,Duan, Kaifei
, p. 141 - 145 (2018/05/25)
A new aza-15-crown-5 derivative 1 bearing coumarin and hydrazone moieties was synthesized and characterized. The fluorescent sensing behavior and selectivity of 1 toward different metal ions in ethanol were investigated. There are 4-fold and 2-fold fluore
Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization and application to enhancement of electroluminescence
Wu, Chia-Shing,Lu, Huai-An,Chen, Chiao-Pei,Guo, Tzung-Fang,Chen, Yun
supporting information, p. 1430 - 1439 (2014/03/21)
Using an environmentally stable metal as the cathode in a polymer light-emitting diode (PLED) is an essential requirement for its practical application. We present the preparation of a water/alcohol soluble copoly(p-phenylene) (P1) containing pendant azacrown ether and ethylene glycol ether groups as a highly efficient electron injection layer (EIL) for PLEDs, allowing the use of environmentally stable aluminum as the cathode. Multilayer PLEDs [ITO/PEDOT:PSS/PF-Green-B/EIL/Al] using P1 as EIL exhibit significantly enhanced device performance, particularly in the presence of K 2CO3 or Cs2CO3. The maximum luminous power efficiency and maximum luminance of the device with Cs2CO 3-doped P1 as EIL were enhanced to 9.16 lm W-1 and 17050 cd m-2, respectively, compared with those without EIL (0.16 lm W -1, 890 cd m-2). The turn-on voltage was also significantly reduced from 5.7 V to 3.7 V simultaneously. The performance enhancement has been attributed to improved electron injection which has been confirmed by the rise in open-circuit voltage (Voc) obtained from photovoltaic measurements. The incorporation of such an electron injection layer significantly enhances device performance for PLEDs with an environmentally stable metal as the cathode.
A fluorene-based material containing triple azacrown ether groups: Synthesis, characterization and application in chemosensors and electroluminescent devices
Wu, Chia-Shing,Lin, Ying-Ju,Chen, Yun
, p. 1419 - 1429 (2014/03/21)
We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) not only for application in aqueous solution as a chemosensor towards Fe3+ but also to enhance the electroluminescence of PLEDs using an environmentally stable aluminum cathode. The photo-physical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy. The FTC exhibited specific selectivity and high sensitivity toward Fe3+, with the Stern-Volmer coefficients (Ksv) being 1.59 × 105 M-1 in a solvent mixture of tetrahydrofuran and water (THF-H2O = 9/1, v/v). The FTC maintained high selectivity toward Fe3+ in the presence of ten interfering metal cations. The HOMO and LUMO levels were estimated to be -5.88 eV and -2.88 eV, respectively. The FTC significantly enhances the emission performance of PLEDs [ITO/PEDOT:PSS/MEH-PPV/EIL/Al] when used as an electron injection layer (EIL), especially in the presence of metal carbonates. Particularly, the device using K2CO3 doped FTC as the electron-injection layer (EIL) exhibited significantly enhanced performance compared to the one without EIL. The performance was significantly enhanced to 11630 cd m-2 and 1.47 cd A-1, respectively, from 230 cd m-2 and 0.03 cd A -1 of the non-FTC device. Current results indicate that multifunctional fluorene-based material FTC is a potential candidate for selective detection of Fe3+ and as an effective electron injection layer to enhance the performance of MEH-PPV.
Substituent group variations directing the molecular packing, electronic structure, and aggregation-induced emission property of isophorone derivatives
Zheng, Zheng,Yu, Zhipeng,Yang, Mingdi,Jin, Feng,Zhang, Qiong,Zhou, Hongping,Wu, Jieying,Tian, Yupeng
, p. 3222 - 3234 (2013/06/27)
A series of new isophorone derivatives (1-5), incorporating the heterocyclic ring or aza-crown-ether group, with large Stokes shifts (>140 nm), have been synthesized and characterized. 1-4 display aggregation-induced emission behaviors, while dye 5 is highly emissive in solution but quenched in the solid state. It was found that the tuning of emission color of the isophorone-based compounds in the solid state could be conveniently accomplished by changing the terminal substituent group. The photophysical properties in solution, aqueous suspension, and crystalline state, along with their relationships, are comparatively investigated. Crystallographic data of 1-4 indicate that the existence of multiple intermolecular hydrogen bonding interactions between the adjacent molecules restricts the intramolecular vibration and rotation and enables compounds 1-4 to emit intensely in the solid state. The size and growth processes of particles with different water fractions were studied using a scanning electron microscope, indicating that smaller globular nanoparticles in aqueous suspension are in favor of fluorescence emissions. The above results suggest that substituent groups have a great influence on their molecular packing, electronic structure, and aggregation-induced emission properties. In addition, fluorescence cell imaging experiment proved the potential application of 5.
Copoly(p-phenylene) containing azacrown ether: Synthesis, optical properties, and application for chemical sensor
Wu, Chia-Shing,Chen, Chiao-Pei,Chen, Yun
, p. 3975 - 3984 (2013/09/02)
Copoly(p-phenylene) (P1) containing pendent azacrown ether and ethylene glycol ether was prepared by the Suzuki coupling reaction and applied for chemical sensor. Poly(p-phenylene) derivative P0 without the azacrown ether groups were also synthesized for comparative study. The photophysical and sensing properties were investigated by absorption and photoluminescence (PL) spectroscopy to elucidate the influence of the azacrown ether groups. The P1 exhibited specific selectivity and high sensitivity toward Zn2+, with the Stern-Volmer coefficient (Ksv) being 3.66 × 106 M-1 at low concentration in mixture solvent of tetrahydrofuran and water (THF/H2O = 9/1, v/v). The P1 maintained high selectivity toward Zn2+ in the presence of fifteen interfering metal cations. This results indicate that copoly(p-phenylene) (P1) is a promising functional material for chemical sensors. Copyright
