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Dyes and Pigments
Elsevier Applied Science Publishers Ltd.
Dyes and Pigments

Elsevier Applied Science Publishers Ltd.

0143-7208

Dyes and Pigments/Journal Dyes and PigmentsSCICCRISTPEIAHCI
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    Highly efficient unbridged D-A~+(D)chromophores based on the quinolizinium cation for nonlinear optical(NLO)applications

    Esmeralda Sanchez-PavonJavier RecioMarco Antonio Ramirez
    14页
    查看更多>>摘要：Novel charged D-A~+ chromophores based on quinolizinium cations as acceptor unit have been prepared by treating haloquinolizinium salts with N-heteroarylstannanes under Stille reaction conditions.This approach provides an easy access to potential one-dimensional D-A~+ and two-dimensional D-A~+-D chromophores in which the acceptor moiety(A~+)is the simple azonia cation and the donors are different π-rich N-heterocycles.The first hyperpolarizabilities(β)were measured by hyper-Rayleigh scattering experiments and the experimental data confirmed that the inherent polarization between donor and acceptor fragments modulates the NLO properties.The electronic structures and properties(including both the linear and nonlinear optical properties)of the quinolizinium chromophores were examined by theoretical(DFT,HF and MP2)calculations.A promising strategy for the rational design of D-A building blocks to create new organic-based NLO materials is proposed.
      原文链接:
    • NSTL

    Development and application of non-conventional luminophores with aggregation based emission

    Hongyang WangBurcu AydinerZ.Seferoglu
    15页
    查看更多>>摘要：Nonconventional luminophores without long conjugated structures have received increasing attention due to their outstanding biocompatibility,easy preparation,environmental friendliness,and potential applications in sensing and imaging.The phenomena of aggregation emission,such as concentration-enhanced emission,aggregation-induced emission,excitation-dependent luminescence,and prevailing phosphorescence,are caused by molecular conformation and molecular packing.Herein,we briefly review the traditional luminophores represented by fused aromatic rings,and introduce the revolutionary concept of aggregation induced emission(AIE)in non-traditional luminescence and its applications in optics,biology,and other fields.The concept of the AIE can be applied to understand this phenomena in the field of non-traditional luminescence,in which non-aromatic systems contain electron-releasing and withdrawing parts,such as amine,amide,nitrile,imine,hy-droxyl,carbonyl,etc.Moreover,we also address two mechanisms of cluster triggered emission(CTE)and crosslink-enhanced emission(CEE).Based on the reviewed data,we can conclude that the electron overlap caused by aggregation and through-space conjugation(TSC)have a profound impact on unconventional luminescence.We believe that this review would serve as a useful guide to design and application of unconventional luminophores,while the current challenges and future perspectives are also discussed.
      原文链接:
    • NSTL

    Phenothiazine metal-organic framework materials with excellent third-order nonlinear properties

    Jianhong JiaMingyan LiJian Wang
    9页
    查看更多>>摘要：The third-order nonlinear optical material with excellent performance is a molecule with a large π-conjugated structure for absorption structure and a high degree of derealization.Nitrogen-sulfur derivatives have lone pairs of electrons in their N and S atoms,which makes them have a strong intramolecular charge transfer ability,which is conducive to the formation of donor-acceptor molecules.In this paper,phenothiazine is used as the matrix structure of the third-order nonlinear optical material,modified,and then metal coordination is performed to obtain[Zn(Py)2Cl2]n and[Cd(Py)2Cl2]n.Its structure is characterized by infrared spectroscopy,single crystal X-ray diffraction and powder X-ray diffraction.The morphology of the material was characterized by scanning electron microscopy.The photophysical properties,thermal properties and third-order nonlinear properties were tested,and the theoretical verification was carried out with the DFT calculation method,and the relationship between the structure and the third-order nonlinear properties was summarized.The experimental results show that phenothiazine has good electron donating ability,the two-photon absorption coefficient(3 is between 1.334-38.400 × 10~(-10)m/W,and the third-order nonlinear polarizability χ~((3))is between 2.752-79.247 × 10~(11)esu,The second-order hyperpolarizability y of the ligand molecule is 5.213 × 10~(-34)esu.The χ~((3))values of[Zn(Py)2Cl2]n and[Cd(Py)2Cl2]n are 4 orders of magnitude higher than ordinary α-quartz(χ~((3))= 2.6 × 10~(-14)esu).
      原文链接:
    • NSTL

    New methylene blue analogues with N-piperidinyl-carbinol units:Synthesis,optical properties and in vitro internalization in human cancer cells

    Bianca StoeanLuiza GainaCastelia Cristea
    15页
    查看更多>>摘要：In this work,two new phenothiazinium dyes containing N-piperidinyl-carbinol auxochrome units have been designed,synthesized and investigated in vitro for ovarian cancer cell fluorescence imaging and cytotoxicity.A solvent free mechanochemical procedure is described as a greener alternative to the previously reported synthetic methodology applied in the preparation of methylene blue analogues by the substitution of the phenothiazinium tetraiodide substrate with nucleophilic secondary amines in solution.The optical properties of the new dyes were evaluated by UV-vis absorption/emission spectroscopy which revealed maxima situated in the red region Omaxabsorption = 668-664 nm and Xmaxemission = 715-698 nm)with large molar extinction coefficients(log e = 4.5-5.1)and bathochromic shifts of 314-383 cm-1 occurring upon switching from less polar to more polar solvents.The theoretical DFT computational study performed in order to clarify the obtained data indicated that the vertical TD-DFT calculations(typically applied for simulating UV-vis spectra)were within-150 nm of the experimental data,but a better agreement with experiment was obtained by using the vibronic corrections which revealed a dominant vibronic component not only for the main absorption/emission maxima,but also for the displayed shoulders which are rather the effects of the vibronic coupling between So and Si electronic states.The new dyes presented a hydrophilic character(logPn.octanoi/water =-1.15 and-1.29 respectively)comparable to the parent methylene blue and no aggregation tendency was observed in aqueous solution at concentration range 75-150 |iM used in this study.Cellular imaging experiments displayed the new dyes'ability to selectively stain the cytoplasm of tumoral OVCAR-3 and A2780 fixed cells.The evaluation of their biological activity encompassed cell grow inhibitory potential(dose-response activity and half maximal inhibitory concentration IC5o),as well as their capacity to influence the tumoral OVCAR-3,A2780 and healthy BJ ovarian cells'metabolic activity.Dye 2 exhibited moderate cytotoxicity against human ovarian cancer cell lines,being the most active against the A2780 ovarian adenocarcinoma cells where its cellular uptake was noteworthy and displayed a deeper influence on the chemoresistant,highly malignant OVCAR-3 cells function by modulating FOLR1,ICAM-1 and VCAM-1 proteins with role in the growth and migration of cancer cells.
      原文链接:
    • NSTL

    Excited-state regulated electroluminescence performance from thermally-activated delayed fluorescence(TADF)to hybridized local and charge-transfer(HLCT)emission

    Xuzhou TianMingming YaoXinqi Liang
    10页
    查看更多>>摘要：In this work,two novel D-π-A compounds(PXZ-FR-DRZ and CZ-FR-DRZ)are designed and synthesized,aiming at the excited-state regulation from thermally-activated delayed fluorescence(TADF)to hybridized local and charge-transfer(HLCT)emission.This change of excited-state nature can be ascribed to the weakened electron-donating ability of carbazole relative to phenoxazine,together with the decreased twisting angle between carbazole and fluorine units.As a result of twisted charge-transfer(CT)excited state,the doped organic light-emitting diode(OLED)of PXZ-FR-DRZ demonstrates a blue-green TADF electroluminescence(EL)with a maximum external quantum efficiency(EQEmax)of 11.5%,while its non-doped device shows a much lower EQEmax.Due to HLCT state of CZ-FR-DRZ,both its doped and non-doped OLEDs achieve the deep-blue non-delayed EL with the satisfied external quantum efficiency(EQE),especially for the excellent efficiency roll-off.Overall,this excited-state transformation between TADF and HLCT allows us to harvest the better comprehensive performance of OLED emitters for the practical applications,which provides a feasible solution for the development of OLED industry.
      原文链接:
    • NSTL

    Design and synthesis of multi-stimuli responsive jc-extended phenothiazine aldehydes:Solvatochromism,acidochromism,moisture detection and fluorochromic sensing of amine vapors1^

    Reshma KumariMarilyn Daisy Milton
    14页
    查看更多>>摘要：A series of phenothiazine-based A-π-D-A type'push-pull'molecules containing sites sensitive to external stimuli was designed and synthesized by phase transfer Heck coupling reaction.A positive solvatochromism was observed with an increase in solvent polarity resulting in an enhanced intramolecular charge transfer(ICT).The existence of TICT was prominent in highly polar media such as methanol and water.Single crystal X-ray diffraction revealed the existence of two structures of VPTZ,with torsional angles of 145.92° and-161.04°,respectively along C-N-S-C plane of the phenothiazine rings.These compounds were used as probes for quantitative measurement of moisture present in three organic solvents,namely CH3CN,THF,and DMSO.The probes could detect moisture as low as 0.0034%(v/v)in CH3CN.Further,these compounds displayed reversible acidochromism in both solution and solid-state.VPTZ,containing pyridine ring as the receptor,displayed excellent sensing of trifluoroacetic acid(TFA)with a detection limit of 91.4 nM.A detailed mechanism involved in reversible acid sensing was studied by 1H NMR.Finally,silica-coated TLC plates were used to fabricate test strips by coating them with VPTZ and then were used as a portable device for selective turn-on sensing of triethyl amine(TEA)and n-dibutyl amine(DBA).TEA and DBA exhibited exceptional fluorochromic turn-on response from purplish-pink to yellow-green and mustard yellow,respectively.
      原文链接:
    • NSTL

    Recent advances in colorimetric and fluorescent chemosensors based on thiourea derivatives for metallic cations:A review

    Sikandar KhanSyeda Aaliya ShehzadiMian Muhammad
    19页
    查看更多>>摘要：Thiourea and its derivatives display several electronic and structural features which enable its application in various fields,ranging from biological to non-biological.These compounds contain heteroatom's like sulfur and nitrogen,which are nucleophilic and allow for establishing inter-and intramolecular hydrogen bonding.In addition,they also provide coordination sites to act as ligands in the field of coordination chemistry.Due to these properties,thiourea derivatives are used as chemosensors to detect various metal cations.This article covers a broad range of thiourea based chemosensors that are used for colorimetric and fluorimetric(turn-off and turn-on)detection of different cations such as Ag~+,Zn~(2+),Cd~(2+),Hg~(2+),Pb~(2+),Mn~(2+),Cu~(2+),Co~(2+),Al~(3+),Cr~(3+),Ga~(3+),In~(3+),Ru~(3+),and Fe~(3+),etc.,in various biological,agricultural and environmental samples.Structural parameters and coordination mechanism of each sensor with metal ions have been discussed.Further,the sensing performances of thioureas derivatives have been compared and discussed,which could help the readers for the future desig of highly sensitive and selective organic fluorescent and colorimetric chemosensors to detect metal cations.
      原文链接:
    • NSTL

    Triphenylamine flanked boron difluoride formazanate for NIR-II fluorescence imaging-guided photothermal therapy

    Hui LiaHanming DaiAnqing Mei
    8页
    查看更多>>摘要：Small molecular theranostic agents play the pivot roles in the biomedical field and hold high clinical translational potential.However,it is still difficult to prepare these theranostic agents through a convenient and straightforward synthetic route.Herein,based on the electron-deficient building block boron difluoride formazanate(BDF),we designed and synthesized a novel NIR-II small molecular fluorescent dye(BDF-Ph)by flanking electron-rich triphenylamine units onto BDF to hamper the intermolecular π-π interaction,thus to achieve high fluorescence quantum yield.Then donor-acceptor-donor(D-A-D)structured BDF-Ph was encapsulated into amphiphilic polystyrene-g-poly(ethylene glycol)(PS-g-PEG)to prepare NIR-II fluorescent BDF-Ph NPs.BDF-Ph NPs possessed an emission peak at 975 nm with a high fluorescence quantum efficiency of 0.32%(IR1061,0 = 1.7%)and a high photothermal conversion efficiency of 40.1%,making it an excellent NIR-II fluorescent probe for nanotheranostics.In vivo investigation illustrated that BDF-Ph NPs exhibited strong NIR-II fluorescence signals.Meanwhile,upon exposure to 808 nm laser,BDF-Ph NPs could eradicate tumors without apparent adverse effects under the direction of NIR-II fluorescence imaging.These fascinating results confirmed that BDF-Ph NPs as an alternative theranostic nanoplatform could be used for oncotherapy.
      原文链接:
    • NSTL

    Reversible thermochromism,two-way mechanofluorochromism and tunable wavelength mechanoluminescence on tetraarylimidazole polymorphs

    Yan-Rong JiaGuan-Lei GaoKai Xu
    8页
    查看更多>>摘要：1,2,4,5-tetraarylimidazole with 4-dimethylaminobiphenyl and 4-cyanophenyl(IMP)respectively introduced at N1 and C2 atom on imidazole core is prepared and two polymorphs correspondingly emit blue(IMP-B)and green(IMP-G)fluorescence are obtained by slow volatilization from solution.The solution-state emission displays the heavily solvatochromic effect as well as the unique solvent-and temperature-dependent LE,ICT and TICT emission equilibrium.X-ray crystallographic analysis,theoretic calculations and temperature-dependent emission decay spectra consistently support the assumption that the emission of IMP-B and IMP-G should respectively originate from LE and TICT state in.crystalline phase.For IMP-G crystal,it displays a reversible theromochromism by annealing-cooling cycles.Under force stimuli,IMP-B and IMP-G crystals present red-and blue-shifted MFC activity.The ground sample selectively pass through the two different routes to be recovered into the original crystalline phase,including transformation into IMP-B by annealing and into IMP-G by vapor fumigation.In spite of centrosymmetric space groups in both crystals,they still exhibit bright ML emission whose wavelength is nearly identical to that of fluorescence on each crystal.It is deduced that polar couples packed by molecules in two crystals may well account for the ML effect on the double polymorphs.
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    • NSTL

    Effect of UV,pH and solvent on the photophysical properties of novel xanthylium fluorophore in solid and liquid state

    Ramalingam ManivannanSi Hyeong ParkHyeon Oh
    10页
    查看更多>>摘要：The current work describes the comparative study of the photophysical properties of new series of xanthylium fluorophore in different organic solvents,the effect of pH,and the effects of UV light irradiation and stability.The designed molecule plays a significant role in the stability.We disclosed the synthesized molecule's stability from UV-Vis,fluorescence,theoretical studies,the molecule sensitivity to solvent polarity,and pH due to its structural nature.The decrease in absorbance and fluorescence intensity with UV-visible light irradiation for the solid and liquid samples were studied.The dye discoloration rate was estimated.The mechanism for the same has been explored,and the information is given in detail.The electrostatic potential,surface mapping analysis,and the stability of the synthesized dye molecules were studied theoretically and compared with the experimental outcome.The stability study and other factors allowed us to predict the suitable application of the synthesized xanthylium fluorophore.
      原文链接:
    • NSTL