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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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    Benzotriazole-based multidonor-acceptor systems as attractive two-photon absorption dye platforms

    Benitez-Martin, CarlosDonoso, BeatrizTorres-Moya, IvanHerrera, Jesus...
    7页
    查看更多>>摘要：Pyrazine-decorated benzotriazole cores allow the orthogonal combination of two dipolar systems within a single molecule. A series of this type of derivatives was synthesized and their photophysical features were studied. The properties of these compounds showed remarkable differences in function depending on the substitution in the pyrazine ring of the benzotriazole core. Furthermore, the two-photon absorption property (2PA) was studied to determine the structure-properties relationship for the reported compounds. The best dye achieved a crosssection of 1532 GM, which was higher than values previously obtained for similar D-pi-A-pi-D benzotriazole derivatives. TD-DFT calculations, which supported the experimental observations, indicating the interaction between the two dipolar systems was responsible for enhancing the 2 PA properties and favoring bathochromic shifts.
      原文链接:
    • NSTL
    • Elsevier

    Harnessing aggregation-induced emission property of indolizine derivative as a fluorogenic bioprobe for endoplasmic reticulum

    Kim, WookChoi, JunwonKim, JonghoonKim, Eunha...
    8页
    查看更多>>摘要：For fluorogenic bioimaging of the endoplasmic reticulum, a new aggregation-induced emission luminogen (AIEgen) core skeleton was conjugated with glibenclamide. Click chemistry was successfully employed for the efficient conjugation between azide-modified glibenclamide and alkyne-containing indolizine core skeleton to generate Aru68. When the volume fraction of water is increases in the solution of Aru68 in water and DMF induced aggregates formation and simultaneous increase of fluorescence intensity up to 100-fold was observed. Solvatochromism and restriction of molecular motion study by perturbation of solvent polarity index and volume fraction of glycerin in glycerin/methanol mixture provided a mechanistic insight into the turn-on phenomenon of Aru68 as AIEgen. The final bio-imaging demonstration of Aru68 in live cell conditions revealed great potential not only of the probe for wash-free bioimaging of the endoplasmic reticulum but also of the indolizine core skeleton for efficient fluorogenic bioprobe development based on aggregation-induced emission processes.
      原文链接:
    • NSTL
    • Elsevier

    N,O-bidentate ligands-based salicylic spiroborates: A bright frontier of bioimaging

    Lugovik, Kseniya I.Fomin, Timur O.Minin, Artem S.Pozdina, Varvara A....
    13页
    查看更多>>摘要：A new series of salicylic spiroborate complexes (SSBs) based on N,O-bidentate 2-(tert-cycloalkylamino)-5-(3-(arylamino)acryloyl)thiophene-3-carbonitriles (NO-SSBs) was obtained and characterized. The optical properties of these compounds were studied and compared with those of analogous BF2-based complexes. The geometries and electronic structures of the NO-SSBs in the ground and excited states, especially their key N-B-O link, were revealed using quantum chemical calculations and compared with the experimental data and photophysical characteristics. Hydrolytic dissociation and photodissociation were considered, and the effects of the NO-SSB structure and nature of the solvent on these reactions were established. Biological investigations elucidated the NO-SSBs ability to penetrate living and fixed cells and selectively accumulate in the endoplasmic reticulum (ER) and Golgi complex. Comparison of the NO-SSBs' characteristics with those of a commercial dye demon-strated the superiority of their properties and prospects for application in the bio-visualization of the ER and Golgi complex.
      原文链接:
    • NSTL
    • Elsevier

    Pyridine derivatives as candidates for selective and sensitive fluorescent biosensors for lung cancer cell imaging and iron ions detection

    Topa-Skwarczynska, MonikaSzymaszek, PatrykFiedor, PawelChachaj-Brekiesz, Anna...
    14页
    查看更多>>摘要：A series of 2-amino-4,6-diphenyl-pyridine-3-carbonitrile (APC) derivatives has been synthesized and their applicability for the role of fluorescent molecular sensors for chemical and biochemical applications has been evaluated. It has been found that the dimethylamino-substituted APC derivatives exhibit a very high solvatochromic effect, that makes them good candidates for application as chemosensors of polarity changes. The fluorescence intensity and emission wavelength of some of the derivatives turned out to be very sensitive to trace amounts of Hg2+, Hg22+, Sb3+ and Bi3+ ions, while other derivatives are selectively sensitive to the presence of Fe2+ and Fe3+ ions. Hence, these derivatives can be applied for the determination of those ions concentration in various media, such as waste water, food products or contaminated soils. Moreover, the applicability of the sensors studied for living lung cancer cells imaging was assessed. It has been found that all of the APC derivatives show good photostability under irradiation conditions used in fluorescence microscopy, while their response is not affected significantly by changes in temperature. Additionally, MTT assays indicated that these sensors were safe for the living cells. So, some of the derivatives studied may be applied for fluorescent staining of the living cells to enable their visualization by fluorescence microscopy.
      原文链接:
    • NSTL
    • Elsevier

    Bithienopyrroledione-based polymeric donors for efficient fullerene- and non-fullerene-based organic photovoltaic cells

    Ha, Jong-WoonPark, Hea JungKang, In-NamHwang, Do-Hoon...
    7页
    查看更多>>摘要：Thienopyrroledione (TPD) is a promising electron-accepting core building block of donor-acceptor-type semiconducting polymers for use in high-performance organic photovoltaic (OPV) cells. In this study, bithienopyrroledione (biTPD) derivatives with different lengths of side alkyl chains were designed to utilize specific ability including stronger electron-withdrawing strength and extended pi-conjugation compared with the mono TPD unit. The synthesized copolymers, poly(3-(5-(4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b'] dithiophen-2-yl)-6-octylthieno[3,2-b]thiophen-2-yl)-5,5'-bis(2-butyloctyl)-3'-(6-octylthieno[3,2-b]thiophen-2-yl)-4H,4'H-[1,1'-bithieno[3,4-c]pyrrole]-4,4',6,6'(5H,5'H)-tetraone) (PBDT-biTPD(BO)) and poly(3-(5-(4,8-bis (5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophen-2-yl)-6-octylthieno[3,2-b]thiophen-2-yl)-5,5'-bis (2-hexyldecyl)-3'-(6-octylthieno[3,2-b]thiophen-2-yl)-4H,4'H-[1,1'-bithieno[3,4-c]pyrrole]-4,4',6,6'(5H,5'H)-tetraone) (PBDT-biTPD(HD)), composed of biTPD and typical benzo[1,2-b:4,5-b']dithiophene (BDT) units had broad absorption with deep frontier molecular orbital energy levels. In addition, PBDT-biTPD(BO) and PBDTbiTPD(HD) showed predominant face-on orientation confirmed by the grazing-incidence wide-angle X-ray scattering (GIWAXS). The OPV device exhibited the maximum power conversion efficiency (PCE) of 8.48% and 8.99% for PBDT-biTPD(BO):PC71BM and PBDT-biTPD(HD):PC71BM, respectively, with a high open-circuit voltage (VOC). In particular, PBDT-biTPD(HD):IT-4F showed the best PCE of 9.49% with improved shortcircuit current, despite the slightly decreased VOC compared to that of PBDT-biTPD(HD):PC71BM.
      原文链接:
    • NSTL
    • Elsevier

    The triple-stimuli-responsive luminescence switching properties and application of a square-planar platinum(II) complex

    Su, MengmengLiu, ShuqinZhang, JianjunMeng, Changgong...
    9页
    查看更多>>摘要：A new square-planar platinum (II) complex, Pt(Me3SiC=CbpyC=CSiMe3)(C equivalent to CC6H4-Me-4)(2 )(1) was synthesized and characterized. This complex has a series of metastable structures, including seven orange solvated species, red 1.1/2(ClCH2CH2Cl), dark-brown 1B, black 1.1/4(CH2Cl2) and 1.1/2(CH3OH), red-brown 1H and solvent-free amorphous 1G. Among them, 1B, 1H, 1G, 1.1/4(CH2Cl2) and 1.1/2(CH3OH) display the long-wavelength NIR luminescence with emission beyond 900 nm. Complex 1 exhibits interesting triple-stimuli-responsive luminescence switching properties. First, 1 shows the reversible vapochromic and vapoluminescence properties between different metastable structures. Upon heating, all species of 1 change to a same solvent-free sample 1H, which emits the NIR luminescence peaked at 988 nm and can be reversibly converted back to the original species by exposure to specific VOC vapor. Furthermore, 1 also shows reversible mechanoluminescence property that all species of 1 will change to a brown amorphous 1G after grinding with its emission wavelength peaked at 954 nm. Systematic studies revealed that the vapor-, thermo-, and mechanical-grinding-triggered triple-stimuli -responsive luminescence switching property of 1 is due to the structural conversion and resultant changes of the lowest energy excited states. Interestingly, the stacking structure and solvated molecule can influence the responses of metastable structures of 1 to heating or mechanical grinding. In addition, complex 1 can be used for visual recognition of CH3CN and 1,2-dichloroethane vapors as well as the development of simple rewritable data recording device.
      原文链接:
    • NSTL
    • Elsevier

    One-pot synthesis and applications of two asymmetrical benzoxanthene dyes

    Ge, JiechaoZhang, WenjunLee, Chun-SingWang, Pengfei...
    6页
    查看更多>>摘要：Two asymmetrical benzoxanthene dyes (BP-1 and BP-2) were designed and synthesized by a convenient one-step procedure from naphthaldehyde and m-aminophenol precursors. These dyes showed long-wavelength absorption, near-infrared emission (>650 nm), and large Stokes shifts (>90 nm) because of the asymmetrical introduction of the benzene ring into the xanthene structure. BP-1 exhibited high fluorescence quantum yield in organic solvents, whereas BP-2 showed very weak fluorescence due to the photoinduced electron transfer of 9 substituted groups. Cell experiments indicated that BP-1 with crescent-shape structure showed lower cytotoxicity and higher photostability than BP-2 and could rapidly stain RNA in nucleoli at low concentration.
      原文链接:
    • NSTL
    • Elsevier

    Highly efficient non-doped deep-blue OLED with NTSC CIEy and negligible efficiency roll-off based on emitter possessing hydrogen bond and hybridized excited state

    Liu, XinyongLi, JingweiQiu, XuYe, Xiyun...
    7页
    查看更多>>摘要：The efficient deep-blue organic emitters with satisfying National Television System Committee (NTSC) standard Commission Internationale de L'Eclairage (CIE) coordinate of (0.14, 0.08) are indispensable component for full-color organic light-emitting diodes (OLEDs) display. In this work, we designed and synthesized a novel deep-blue material TPIN with donor-pi-acceptor (D-pi-A) structure by utilizing triphenylamine (TPA) as donor, 1,4,5-triphenyl-1H-imidazole (PIM) as acceptor and pyridyl as pi-bridge. The pyridyl is expected to endow TPIN with multiple intra-/intermolecular hydrogen bands (H-bands) interactions which could inhibit molecular vibration and affect the radiative transition, aiming to obtain efficient deep-blue OLED with high color purity and negligible efficiency roll-off. In addition, the photophysical experiments and theoretical calculations were implemented to verify the unique hybridized excited state of TPIN. And X-ray crystallographic analysis of TPIN single-crystal indicates that there exist many C-HN and C-H center dot center dot center dot pi interactions in the stacking structure. The non-doped device based on TPIN exhibited good deep-blue electroluminescence (EL) performance with emission peak at 443 nm, corresponding to a CIE coordinate of (0.151, 0.080), and a maximum external quantum efficiency (EQEmax) of 3.71% with negligible efficiency roll-off (EQE = 3.70% @ 1000 cd m(-2)).
      原文链接:
    • NSTL
    • Elsevier

    Aggregation-induced emission-active fluorescent polymer sensors for the detection of water in organic solvents, Cu2+ and hemolysis

    Liang, WendongLiu, DanHuang, JianbingLiang, Hui...
    8页
    查看更多>>摘要：The hydrophobic polymer HDDA-EDT-SADA with aggregation-induced emission (AIE) property was synthesized via the thiol-ene click copolymerization of salicylaldehyde azine (SA) derivative diacrylate monomer SADA and commercially available 1,2-ethanedithiol (EDT) and 1,6-hexanediol diacrylate (HDDA). HDDA-EDT-SADA was found to display unexpected intense fluorescence in acetone and DMSO compared to that in other good solvents, which dramatically decreased by adding small amount of water. We demonstrate that HDDA-EDT-SADA can be used as a fluorescent sensor for water detection in acetone and DMSO. To improve the water solubility of the AIE-active polymer, SADA was copolymerized with dithiothreitol (DTT) and poly(ethylene glycol) diacrylate (PEGDA) to give an amphiphilic AIE polymer PEGDA-DTT-SADA. Similar fluorescence phenomenon was also found in DMF, suggesting that PEGDA-DTT-SADA could serve as an indicator for water detection in DMF. Thanks to the PEG segments and DTT units, the PEGDA-DTT-SADA was able to well-disperse in water via the formation of stable micelles. The PEGDA-DTT-SADA selectively complexed with Cu2+ and thus could be used as a fluorescent sensor for Cu2(+) detection in aqueous media. Moreover, the PEGDA-DTT-SADA could be utilized as a fluorescent sensor for hemolysis ratio detection of red blood cells (RBCs) due to the inner filter effect.
      原文链接:
    • NSTL
    • Elsevier

    Diazine-based thermally activated delayed fluorescence chromophores

    Achelle, SylvainHodee, MaximeMassue, JulienFihey, Arnaud...
    19页
    查看更多>>摘要：Diazines are electron deficient six-membered aromatic rings heterocycles which have successfully been employed in the design of a wide range of push-pull chromophores for various applications in the field of organic electronics and optoelectronics. For instance, some have been specifically designed to be inserted in the electroluminescent emission layer of organic light emitting diodes (OLED). OLED technology has continuously evolved and is currently used in industry for display and lighting purposes, offering many advantages including low turn on voltage and power consumption. In the prospect to further reduce energy waste, a third generation of OLED based on thermally activated delayed fluorescence (TADF), which allows harvesting both triplet and singlet excitons, attracts increasing attention from the scientific community. In this review, we provide a comprehensive overview of the present status of diazine-based dyes developed for TADF. The pyrimidine core is by far the most used and has demonstrated deep blue, blue or sky-blue and green emission when combined with carbazole, acridan and phenoxazine fragments, respectively. Further design of TADF emitters is desirable to afford red OLED and both the pyrazine and pyridazine cores have been scarcely explored.
      原文链接:
    • NSTL
    • Elsevier