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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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    Large red-shifted NIR absorption in azulenyl-and iodinated-modified BODIPYs sensitive to aggregation and protonation stimuli

    Chunrui ZhaoBin WuJufang Yang
    7页
    查看更多>>摘要：Pushing forward the red-shifting of electronic transitions in organic dyes is potentially important for applications in photodynamical chemistry and therapies. In this work, a series of BODIPY derivatives conjugated with azulene at different substituent positions were synthesized and investigated in depth. These compounds are shown to exhibit varying bathochromic shifts of their electronic transitions, as well as a further red-shift of the absorption by the modification of the compounds with iodine. Moreover, self-assembly and protonation of these compounds lead to hundreds of nanometer red-shifted electronic transitions, up to NIR-II window, relative to traditional BODIPYs. On this basis, a unique photoproduction of singlet oxygen species can be achieved under corresponding long-wavelength irradiation both in organic solution and in water, featuring a superior photosensitivity and photodynamic potential of the molecular design.
      原文链接:
    • NSTL

    Bis(N-naphthyl-N-phenylamino)benzophenones as exciton-modulating materials for white TADF OLEDs with separated charge and exciton recombination zones

    Malek MahmoudiJonas KeruckasDmytro Vblyniuk
    10页
    查看更多>>摘要：Organic semiconductors were employed as exciton modulators, blue emitters, hole-transporting materials and hosts with resonant-appropriate singlet and triplet energies for efficient and stable white organic light emitting diodes (OLEDs). Two 4,4'-bis(N-naphthyl-N-phenylamino)benzophenones were synthesized using isomeric N-naphthyl-N-phenylamines as the donors and benzophenone as the acceptor moiety. Molecular design of new compounds allowed to obtain required combination of properties, i.e. blue prompt fluorescence in solid state with singlet energies close to those of the selected blue emitter exhibiting thermally activated delayed fluorescence (TADF), low triplet energies of 2.32 and 2.45 eV which are close to those of orange TADF emitter, good charge injecting properties (ionization potentials of 5.68 and 5.79 eV), good charge transporting properties with hole mobilities exceeding 10~ cm2 (V s)~(-1) and high thermal stability with five percent weight loss temperatures up to 428 °C. The blue-emitting compounds were used as exciton modulators between the known blue and orange TADF emitters for fabrication of white OLEDs exploiting spatial exciton allocation strategy. In the frame of this strategy, resonant energy transfers: NPABP emitters-blue TADF and NPABP emitters-> orange TADF emitters were investigated using different device structures towards efficient white electroluminescence. About twice higher external quantum efficiency was obtained for devices with two resonant energy transfers in comparison to that of the reference devices with one resonant energy transfer proving efficiency of spatial exciton allocation strategy for white TADF OLEDs. The best quality of white electroluminescence is characterized by CIE coordinates of (0.32, 0.31), colour temperature of 4490 K and colour rendering index of 80. Similar stability of blue and orange emission bands in white electroluminescence spectra was achieved due to the separation of charge and exciton recombination zones in the device structure.
      原文链接:
    • NSTL

    Regioisomeric dipyrazolyl-anthracene luminophores: mechanochromic luminescence switch and mercury ion detection with 'turn-off response

    Zhi-Feng WangJin TongJing Guo
    9页
    查看更多>>摘要：A series of regioisomeric luminophores L1-L8 with lH-pyrazol-3-yl or lri-pyrazol-4-yl substituents at the different positions of anthracene core have been synthesised and characterised. According to the photophysical properties and related frontier orbital features of these compounds, the 'site-effect' of pyrazolyl substituent on an anthracene unit can be found, demonstrating the dependence of the properties of the compound on the position of substitution of the pyrazolyl moieties connecting to the anthracene core. Moreover, the target luminophores present reversible mechanochromism properties. The most significant mechanochromism luminescence is achieved for luminophores LI and L2 with pyrazolyl substituents at the 9-and 10-positions of the anthracene unit. Upon grinding the pristine powder sample, a colour change from light yellow to yellow-green is observed. In addition, the target luminophores L2, L4, L6 and L8 demonstrate sensing properties of Hg~(2+) ions with high selectivity and exceptional sensitivity. These findings suggest that these anthracene-centred luminophores are promising functional platforms with fluorescence and selective heavy metal sensor arrays.
      原文链接:
    • NSTL

    Rapid and colorimetric evaluation of G-series nerve agents and simulants using the squaraine-ethanolamine adducts

    Jiayin ZhaoMolin QinJiawen You
    8页
    查看更多>>摘要：High toxicity and reactivity of chemical warfare agents (CWAs) have attracted increasing demand of reliable detection methods for countering terrorism. Herein, we report a chemical approach based on the squaraine-ethanolamine (SQ-ETA) adducts for rapid, sensitive, and selective detection of the G-series nerve agents and simulants in aqueous media. Present strategy features the merits of obvious turn-on response and colorimetric mode upon the presence of certain analytes. Possible sensing mechanism was the nucleophilic addition of ethanolamine toward the central SQ core to generate a SQ-ETA adduct firstly, supported by the additional NMR and MS characterizations. And special binding affinity of the G-series nerve agents and simulants to the hydroxyl groups in the SQ-ETA adducts thus recover the original SQs (SQOH and SQPY), endowing distinguishable colorless-to-blue change. The detection limits for diethyl chlorophosphate and diethyl cyanophosphonate were determined from the SQOH-ETA system to be 3.5 and 36.0 uM, respectively. In addition, the obtained adducts were further utilized to detect real G-series nerve agents including sarin (GB) and soman (GD), confirming the strategy suitable for on-site detection. In conjunction with smartphone-based analytical methodology, proper correlation between the RGB changes and substance concentrations was founded. Present successful trials inspire the semi-quantitative evaluation of G-series nerve agents with high accuracy and relative simplicity, implying great potential in detecting CWAs.
      原文链接:
    • NSTL

    Hemicyanine-based turn-off fluorescent probe for monitoring of nitric oxide in living cells

    Yong ZhangChengli JiaYuesong Wang
    9页
    查看更多>>摘要：In situ imaging of nitric oxide (NO) is of great importance to study the critical roles of NO in various physiological and pathological processes. In most currently available fluorescent probes for NO, the o-phenylenediamine (OPD) based derivatives are the most greeted and studied, in which the OPD serves as the reactive site and fluorescence quencher to modulate a turn-on process via photoinduced electron transfer (PET). In this work, a unique turn-off probe containing OPD moiety, N-l, was designed and synthesized, which was radically different from the typical PET-based turn-on fluorescent probes. By theoretical calculation of molecular orbital, it was verified that not the widely used PET mechanism, but the intramolecular charge transfer (ICT) mechanism should be responsible for the turn-off process. Probe N-l exhibited a remarkable performance with 7-folds fluorescence intensity decrease (at 490 nm), a low detection limit (20 nM), a fast response to NO within 12 min and a high selectivity for NO over other relevant analytes. Furthermore, probe N-l was also applied to imaging NO in living cells. All results demonstrated that the new probe N-l could be a practical and ideal NO indicator with good biological significance.
      原文链接:
    • NSTL

    A cyanine-type homolog of the red hair bibenzothiazine chromophore combining reversible proton-sensing with a hydrophobic-to-hydrophilic switching response

    Orlando CrescenziMaria Laura AlfieriLucia Panzella
    9页
    查看更多>>摘要：A2,2-bi-(2H-l,4-benzothiazine) chromophore of trichochrome pigments occurring in red hair and feathers has been recognized as a source of inspiration for the design of functional chromophores given its excellent photochromic, solvatochromic, and acidichromic properties. Here we report the synthesis of a symmetric homolog of the bibenzothiazine system produced by condensation of 3-phenyl-2H-l,4-benzothiazine with glyoxal that was assigned the cyanine-type 22,2'2-(l,2-ethanediylidene)bis(3-phenyl-2H-l,4-benzothiazine) (1) structure by spectral analysis and DFT calculations. The cyanine showed an intense absorption maximum at ca. 480 nm (e = 16.070 ± 60 M~(-1)cm~(-1)) in 3:1 methanol/water at pH > 4.0 undergoing a marked bathochromic shift in acid to 610 nm (e = 22.330 ± 40 M~(-1)-cm~(-1)), and further shift to 637 nm in 2.5 M HC1 accompanied by a distinct color change from red to deep blue. The bathochromic shift upon exposure to acids was observed on fabrics, paper, polylactic acid films or alginate hydrogels as well as on thin films of the cyanine exposed to acid/basic vapors and proved reversible over several cycles. The acidichromic behaviour was associated to a remarkable hydrophobic-to-hydrophilic switch, that was probed in a filter permeability experiment. Other applications that are presented for the cyanine include the use as pH sensor paper for visual assessment of pHs below 0 and devices for monitoring food freshness, e.g detection of volatile amines generated by fish spoilage or pH changes associated to milk deterioration.
      原文链接:
    • NSTL

    Spiro-type TADF emitters based on acridine donors and anthracenone acceptor

    Dongwook YangJin-Suk HuhJong-In Hong
    6页
    查看更多>>摘要：Two rigid spiro-type TADF emitters (CBZANQ, PXZANQ) were designed and synthesized via a two-step route. CBZANQ and PXZANQ both contain a,n anthracenone acceptor along with a carbazole-acridine-fused donor and a phenoxazine-acridine-fused donor, respectively, where each donor and acceptor are linked by a spiro bridge to form D-c-A structures with an orthogonal arrangement. Both CBZANQ and PXZANQ have the difference between the singlet and triplet energy values (AEst) of 0.05 eV and 0.03 eV, respectively, which are sufficiently small for efficient triplet harvesting. CBZANQ with a weak electron donor (carbazole) exhibited a weak intramolecular charge transfer (ICT) character, resulting in a low photoluminescence quantum yield (PLQY) of 18%. On the other hand, when combined with a strong electron donor (phenoxazine), PXZANQ exhibited a strong ICT character, resulting in a high PLQY of 71%. Organic light-emitting diode (OLED) devices based on CBZANQ emitter and bis[2-(diphenylphosphino)phenyl] ether oxide (DPEPO) host exhibited sky-blue electroluminescence (EL) at 492 ran with a low external quantum efficiency (EQE) of 6.7%. Conversely, the OLED devices fabricated using PXZANQ emitter and DPEPO host exhibited green emission at 528 ran, along with a high EQE of 22.1%. Additionally, the efficiency of PXZANQ-based devices remained high at high luminance, indicating relatively small efficiency roll-off (13.9% EQE under 500 cd/m2).
      原文链接:
    • NSTL

    Ratiometric fluorescence assay for butyrylcholinesterase activity based on a hemicyanine and its application in biological imaging

    Chenyang WanJiajia LiJian Gao
    8页
    查看更多>>摘要：Butyrylcholinesterase (BChE) is an esterase expressed by the liver, which is released into the plasma immediately. The activity of BChE in the serum is a sensitive indicator for determining the protein synthesis function of liver cells. Therefore, the development of high-efficiency chemical tools for detecting BChE is in urgent need. In this work, based on the ingenious combination of specific BChE enzymatic reaction, a ratiometric fluorescence probe was established to easily achieve the determination of BChE with high sensitivity with LOD calculated as low as 0.077 ug/mL. This probe also possesses a superior selectivity to BChE without the interference of other biological species even acetylcholinesterase (AChE), which gives it great potential to work for sensing in biological samples. The accurate IC50 (0.195 mM) of iso-OMPA, a specific inhibitor of BChE, could also be examined, indicating the excellent performance in elucidating inhibitory efficacy. In addition, the probe can be used for fluorescence imaging of BChE activity in living cells as well as animal tissues. These advantages indicate that the probe has important practical value for the monitoring of BChE activity.
      原文链接:
    • NSTL

    Cucurbituril-mediated AIE: An unconventional indicator displacement assay for ketamine detection

    Kun YanLancheng WangHuimin Zhou
    8页
    查看更多>>摘要：Typical AIE luminogens with extensive Jt-electron conjugation are limited in use on account of their complex synthesis, high cost and environmental concerns. To this end, we report here a novel host-guest inclusion complex that is assembled from nonemissive ligands, and surprisingly exhibits notable AIE features in aqueous solution while maintaining good sensitivity for ketamine (KET) detection. Isothermal titration studies confirm that palmatine (PAL) binds to cucurbit[8]uril (Q8) in a 2:1 ratio with an equilibrium association constant of 1.75 x 10~(11) M~(-2), suggesting that the unconventional AIE effects can be attributed to the stacking of two PAL moieties inside a single Q8 cavity. Geometric constraints of the macrocycle result in dimeric coupling of PAL in the ground state with significant bathochromic shifts in absorption and emission, which can be readily excited to exhibit enhanced photoluminescence. The unusual upfield perturbation and broadening of Q8 signals in the ~1H NMR spectrum upon binding with PAL convey decisive information that Q8 not only serves as a molecular container, but also participates in the electron derealization during the AIE events. Upon addition of KET, fluorescence was switched off through guest exchange to generate KET@Q8 as well as free PAL. The significant AIE characteristics of 2*PAL@Q8 in combination with its specific molecular recognition towards KET gives rise to 5.0 ng/mL limit of detection with linear range from 16.8 to 500 ng/mL, and a pronounced selectivity over possible interfering substances in biological matrices. We demonstrate the first example of Q8-mediated AIE effects, where the photoluminescence of virtually nonemissive or feebly emissive ligands is remarkably intensified through clustering inside a macrocyclic host molecule, therefore offering great promise for further development into dedicated AIE-based sensors.
      原文链接:
    • NSTL

    Novel wide bandgap benzodithiophene-based polymer donors with electron-withdrawing indolin-2-one side chains for efficient organic solar cells with high open circuit voltage

    Wuqi LiMarwa Abd-EllahHaitao Liu
    9页
    查看更多>>摘要：Two new Ji-conjugated polymers with donor backbone and jt-conjugated indolin-2-one side chains, PBDTTI and PBDTTIF, are designed and synthesized as wide bandgap donors for non-fullerene acceptor-based organic solar cells (OSCs). The monomers containing electron accepting indolin-2-one side chains, (Z)-3-((2,5-dibromothio-phen-3-yl) methylene)-l-methylindolin-2-one (Ml) and (Z)-3-((2,5-dibromothiophen-3-yl) methylene)-5-fluoro-l-methylindolin-2-one (M2), can be easily synthesized via Knoevenagel condensation between 2,5-dibromothio-phene-3-carbaldehyde and 2-oxindole or 5-fluoro-2-oxindole, respectively. Stifle coupling polymerization of the electron donating benzodithiophene (BDT)-containing monomer l,l'-[4,8-bis [5-(2-ethylhexyl)-2-thienyl]benzo [l,2-b:4,5-b']dithiophene-2,6-diyl]bis [1,1,1-trimethylstannane] and Ml or M2 produced PBDTTI or PBDTTIF, respectively. The strong electron accepting jt-conjugated l-methylindolin-2-one and 5-fluoro-l-methylindolin-2-one side chains can achieve low-lying HOMO energy levels of-5.59 eV for PBDTTI and-5.60 eV for PBDTTIF, which is beneficial for realizing high open circuit voltage (Voc) of the resulting OSCs. On the other hand, since the electron acceptor units are on the side chains, the polymer backbone containing only electron donor units could maintain wide bandgaps of 1.91 eV and 1.89 eV for PBDTTI and PBDTTIF, respectively. When PBDTTI and PBDTTIF were used as donors and a small bandgap non-full acceptor ITIC as an acceptor, the resulting OSCs devices achieved Voc of 0.97 and 1.00 V, short circuit current densities (J_(se)) of 15.60 and 13.70 mAcm'2, and fill factors (FF) of 0.60 and 0.59, resulting in power conversion efficiencies of 8.00 and 7.70%, respectively.
      原文链接:
    • NSTL