Synthesis and multicolor luminescent properties of polystyrene side-chain difluoroboronabobenzone complexes (2023)

Table of Contents
dyes and pigments Abstract Graphical summary present partial fragment Measurement Optical properties of ABSt in solution and solid state in conclusion Declaration of competing interests Thanks report(45) Determination of histamine in rat brain microdialysis samples by microporous liquid chromatography after intramolecular derivatization of a pyrene-labeled reagent Journal of Neuroscience Methodology Tuning the solid emission color of polymers composed of different ratios of BODIPY and styrene pigment Significant difference in crystal fluorescence lifetime of dibenzoylmethane boron difluoride and its diisopropyl derivative Tetraedarski Wright Polymerization-induced luminescence: glow together, float together! chemical examination Polymers containing dyes: Preparation of mechanochromic materials chemical society review Intracellular fluorescence temperature probe based on triarylboron-substituted poly(n-isopropylacrylamide) and energy transfer anal chemistry Re-understanding the fluorescence behavior of tetracoordinate monoborate complexes containing monoanionic bidentate ligands Journal of Physical Chemistry B Molecular interactions in organic nanoparticles for application in phototherapy chemical examination The fluorescence properties of aggregates of pyrene derivatives formed in polymer matrices depend on the concentration physical chemistry chemical physics A novel self-assembly platform for analog fluorescence detection of spermine chemical company Highly Selective Fluorescence Derivatization of Polyamines Based on Intramolecular Eximer Formation Production of Pyrene Labeling Reagents anal chemistry Photophysics of hypercorrelated pyrenes in aqueous polymer solutions and other organized media chemical examination Color-tunable photoluminescence and a cavity-mediated multistage energy transfer cascade ACS Nano Color-tunable solid-state fluorescence emission from carbazole-based bodipys European Journal of Chemistry Understanding the spectral properties and aggregation process of the new luminescent boron dipyromethane (bodipy) Journal of Physical Chemistry Fine Tuning of Yellow or Red Photoluminescence and Electroluminescence of Difluoroborodiazabiphenyl Functional Thin Films Advanced functional materials Bodila and their derivatives: composition and spectral properties chemical examination Concentration-dependent fluorescence color tuning of difluoroborobobenzone complexes in polymer films Chemical Society of Japan Bull Substituent-Dependent Reverse Reaction of Mechanofluorescence Chromogenicity of Dibenzoylmethane Boron Difluoride Derivatives photochemical photobiological science Difluoroboronaphthylphenyl β-diketone polylactide materials: effects of heavy atom arrangement and polymer molecular weight Macromolecule Direct visualization of the two-step nucleation model with fluorescence color changes during solution evaporation crystallization representative of science Polymorphic, mechanofluorochromatic and photophysical characterization of carbonyl-substituted difluoroboron-β-diketone derivatives Journal of Physical Chemistry Reported by (7) from BF2- Polymer to smooth the modification effect after chelation and Eu3+- Setting the color of metal polymers Synthesis of Diylethylene Derivatives with Dibenzoylmethane Boron Difluoride Complex and Its Fluorescent Optical Switch Motion as a fluorescence probe for assembly processes involving high-density liquid-like intermediates during evaporative crystallization Polydimethylsiloxane grafted with dibenzoylmethane boron difluoride: synthesis and properties Molecular aggregation dynamics through liquid-like interstitial clusters during heterogeneous evaporation revealed by hyperspectral camera fluorescence imaging Boron difluoride hydrazone polymer (BODIHY) exhibits aggregation-induced luminescence Featured Articles (6) Predictors of improved endothelial function in patients with mild hypertriglyceridemia without evidence of coronary artery disease treated with pure eicosapentaenoic acid Microsurgical or endovascular strategies for complete removal of vertebral arteriovenous shunts in a 10-year retrospective single-institution study Enhanced cancer suppression by miR-143 with a longer passenger chain than natural miR-143 Aortic and pulmonary valve reconstruction using autologous pericardium in a stenotic annulus Nonlinear interaction between bulk vortex and interface in incompressible Richtmyer-Meshkov instability Membrane transitions from specific groups

dyes and pigments

volume 177,

June 2020

, 108283

The author link opens an overlay panel, , , ,

Abstract

symptomaticCopolymer(Polish (ABSt-cooperative-St)) consists of Avobenzone-BF2complicatedunilateral(ABSt) and styrene (St) were synthesized and used to tune emission colors, including solid-state white emission, fromYingshiunits as intervals. By changing the content of St, the emission color of ABSt in the obtained copolymer changed from green to blue-white to blue-white. fluorescencequantum yieldRelatively high content of solid polymers (Phieat=0.30–0.51) regardless of composition. Polymers have two main emission bands around 440 and 540 nm, which originate from individual molecules andamorphousConcentrated, that is. The fluorescent color changes depending on the scaleFluorescence intensity440 to 540 nm (eat440/eat540).Absorptive and fluorescent properties of polymersTetrahydrofuranregardless of the ABSt to St composition ratio, suggesting no intermolecular interaction between avobenzone-BF2(AB)Fluoroforwithin the polymer chain. The emission color of all polymers in solution is blue,Fluorescence spectroscopySame as ABSt in solution. Therefore, the emission color change observed in the solid state mainly results from the intermolecular interactions between the AB fluorophores in the interpolymer chains, as the polymers are interwoven with each other in the solid state. When a solid polymer is annealed,eat440/eat540Depending on the arrangement of the polymer chains, the lift-off and overall fluorescence spectra become similar to those emitted by the monomers. It can be concluded that the color change of the polymer mainly originates from the intermolecular interactions between the AB fluorophores in the chains between the polymers. We showed that poly(ABSt-cooperative-F) form an excellent uniform fluorescencethin polymer filmIn contrast, mixtures of methoxy AB(ABOMe) and poly(St) crystallized even at low ABOMe content in poly(St).

present

In recent years, light-emitting molecules that exhibit changes in emission properties with changes in concentration and environment have attracted much attention for applications as sensor materials [ [1] , [2] , [3] , [4] , [5 ] ] . For example, pyrene derivatives are known to form highly excimers derived from molecules in the condensed state and emit fluorescence in the longer wavelength region [ [5] , [6] , [7] , [8] , [9] , [ 10 ]]. Fluorophores with high flatness and low Stokes shift, such as borodipyrromethane (BODIPY) derivatives, also exhibit green-red emission through self-quenching and dimer formation [11] , [12] , [13] , [14] , [15] ], [16]]. Difluoroborabobenzone (AB) complexes are known to emit light in the solid state and shock) exhibit mechanochromism [ [17] , [18] , [19] , [20] , [21] , [22] [23] , [24] ]. It has been reported that mechanochromic properties are caused by changes in molecular arrangement and a phase transition from a crystalline to an amorphous state. Ito and co-workers used spectroscopic and image analysis to reveal the assembly process of AB during solution evaporation [20]. This process can be explained by a two-step nucleation model from the solution state through the amorphous state to the crystalline phase. Ikeda and co-workers also reported the effect of substituents and filling mode on the fluorescence properties of various AB derivatives [25,26]. Chujo and co-workers focused on boron-containing polymers because of their outstanding properties, such as high charge carrier mobility, excellent optical properties, high stability, and high processability. In particular, they reported the tuning of emission color and brightness of polymers containing boron complexes (such as boron diketoate or boron diimide) in the main chain and side chains [27], [28], [29], [30]. ].

Nowadays, the preparation of white light emitting materials has received attention due to their potential applications in lighting devices and display media [31], [32], [33], [34], [35], [36], [37]. ] , [ 38], [39], [40], [41]. In general, white emission requires a combination of the three primary RGB colors (red, green, blue) or at least two complementary colors in appropriate composition ratios. If white emission can be achieved using a single fluorophore, the material will hold promise for practical applications. To date, several white emission methods using a single fluorophore have been published [42], [43], [44], [45]. However, the emission of white light from a single molecule is still rare, and creating a white light-emitting material composed of a single fluorophore remains a challenge.

Here, we focus on the dual emission of blue (monomer) and yellow-green (amorphous) AB and the ability to produce white emission by combining their phases at appropriate feed ratios. However, AB sometimes crystallizes even in the polymer because the high planarity of the avobenzone moiety leads to high crystallinity. In this work, we report random copolymers (poly(ABSt-cooperative-St)) is composed of AB monomer (ABSt) and styrene (St), using St as a spacer to achieve multicolor and white emission in the solid state, as shown in Figure 1. Optical properties of poly(ABSt-)cooperative-St) in different media, such as solutions, bulk powders, and bulk films, are also discussed in this article.

partial fragment

Measurement

Spectroscopic grade solvents were purified by distillation before use.1'H NMR (300 MHz) i13C NMR spectra (75MHz) were recorded on a BRUKER AV-300N spectrometer using tetramethylsilane (TMS) as internal standard. Infrared (IR) spectra were recorded on a JASCO FT/IR-4100 spectrometer. Mass spectra were obtained using a Bruker FT-ICR/solariX mass spectrometer. Elemental analysis was performed using a J-SCIENCE LAB JM10 CHN Analyzer Micro Corder. Differential Scanning Calorimetry (DSC)

Optical properties of ABSt in solution and solid state

Basic optical properties of ABSt, e.g. UV-Vis. The absorption spectrum includes the molar extinction coefficient (electronic) and fluorescence spectra at a concentration of 1×10−5M in THF, as shown in Figure S3. ABSt has a maximum absorption at 374nm and aboveelectronic(55700 M−1centimeter−1) wave length. Two main emission bands at 407 and 427 nm and a high fluorescence quantum yield (Phieat=0.66). In addition, the dependence of emission characteristics on ABSt concentration

in conclusion

Polished (ABSt-cooperative-St) were synthesized and their emission properties were studied. Multicolor fluorescent materials with white emission have been successfully prepared using a single fluorophore. Poly(ABSt-cooperative-St) (entry 2) shows light emission (Phieat=0.46) and near pure white CIE (0.27, 0.35) (0.33, 0.33). The color change of the polymer was shown to be caused by intermolecular interactions between the ABSt fluorophores and not within the polymer

Declaration of competing interests

The authors declare that they have no known financial interests or personal relationships that could influence the work reported in this article.

Thanks

This work was supported in part byJSPS Avatarcredit numberJP26107013(S. Kobatake)JP17H05253(F. egg) uScientific research on "photosynthesis" in the field of innovationIJP19H02686(F. egg) uScientific research (2)The authors (K. Shimizu and S. Kobatake) also thank the SiMS at MEXT, Japan, Osaka Prefectural University/Osaka City University Leadership in Graduate Program for Materials Science Leaders.

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