Solid-stated smart polymers responsive to external stimuli have attracted much attention for potential application in the field of photoelectron devices, logic gates, sensor, data storage and security. However, it is a bigger challenge for polymers than that for small molecules in solid state to acquire stimuli-responsive properties, because polymers with high molecular weight are not as easy to change the packing structure as small molecules under external stimulation. Here, a D-A type alternating copolymer PTMF-o containing 3,4-bisthienylmaleimide (A unit) and fluorene (D unit) is designed and synthesized. Upon irradiation of sunlight, PTMF-o film exhibits a photo-response with the color altering from purple to colorless. It is attributed to the structure of copolymer transformed from ring-opening form (PTMF-o) to ring-closure form (PTMF-c), resulting from the oxidative photocyclization of 3,4-bisthienylmaleimide unit. Consequently, the ability of charge transfer (CT) from fluorene to 3,4-bisthienylmaleimide unit in PTMF-o can be easily weakened by light stimuli. PTMF-o film displays a WORM-type resistive storage performance for the strong CT. Interestingly, after exposure, the electrical memory behavior in situ transfers into FLASH type, due to weak CT in PTMF-c. PTMF-o film can also be employed as smart material to construct NAND and NOR logic gates by using light as input condition. The work provides a simple way to modify the electronic properties of polymers and realize stimuli-response in solid states.
A simple organic molecule displays both mechanoluminescence and room-temperature phosphorescence switching. A D–A type dimer is found to be responsible for the switching.
Bisindolylmaleimide derivatives (IMs) were found to be sensitive to different anions in various solvents, and utilized to construct five logic devices.
Full-solution processed, flexible, top-emitting polymer light-emitting diodes (PLEDs) are fabricated by using low-cost and high-quality printed Ag electrodes. Employing a composite cathode (Ag/ZnO/PEI) and bi-layer anode ofWO(3)/PH1000, the resulting devices exhibit quite comparable device performances to the conventional PLEDs, remarkable flexibility and great potential for large-area production.
Novel maleic anhydrides symmetrically substituted by two aromatic rings exhibit distinct emission behaviours: aggregation-caused quenching (ACQ), aggregation-induced emission (AIE), and dual-state emission (DSE) in both solution and the solid state. Appropriate modifications were made to turn ACQ/AIE into DSE and realize full-color DSE.
Intensely emissive diarylmaleimides PM and TM were introduced into the backbone of polyfluorene (PF) to obtain single white polymers, PFPM and PFTM. PFPM showed highly efficient and white electroluminescence for effective energy transfer from the PF host to the maleimide guest.
A simple solvent annealing method was utilized in the inverted planar PVSCs with a structure of ITO/PEDOT:PSS/MAPbI3/PCBM/Ca/Al. The optimized MAPbI3 active layer not only endowed the increased PCE but also the highly reproducible and photocurrent hysteresis-less properties to the devices.
A series of carbazole-based diphenyl maleimide dyes with different N-substituent were synthesized through an Ullmann reaction in high yields. The dyes exhibit an intense emission in the solid state for their twisted conformation fixed by weak intermolecular interactions, resulting in the hindrance of the internal rotations. Their solid-stated emission wavelength and intensity are sensitive to external stimuli (like heat, pressure and vapor), due to a crystal-to-crystal or crystal-to-amorphous phase transition. Based on the multi-stimuli-responsive fluorescence properties of the N-benzyl analogue, two kinds of applications were explored. One is rewritable data recording processes including solvent writing and vapor writing. The other is sensing for low hydrostatic pressure (0-25 MPa). Interestingly, nanoparticles of the dyes formed in aqueous solution could effectively detect explosive and pH changes. A 15 ppm concentration of picric acid quenched the fluorescence of the N-methyl analogue with the detectable limit calculated to be 0.13 ppm. The N-methyl analogue also showed a different emission color and intensity over the pH range 12-14, which originated from the hydrolysis of the dye molecules in the strongly basic solution. (C) 2016 Elsevier Ltd. All rights reserved.
A series of new CIE-active diphenyl maleimide derivatives with multi-stimuli-responsive fluorescence were reported. Three kinds of new technologies for rewritable information storage and security ink were developed by using their multi-stimuli-responsive fluorescence.
A novel Λ-shaped donor–π–acceptor–π–donor molecule BCPMM with AIEE, CIEE and polymorphism-dependent fluorescence properties was utilized to construct five simple logic gates and more than ten kinds of sequential combinational logic systems.
有机绿色荧光材料由于在分子识别、生物探针和电致发光领域具有广泛的应用而备受关注.本文以苯乙腈为原料,在甲醇钠的催化下,合成了3,4-二苯基马来酰亚胺中间体,并在在碱性条件下,将苄基引入到马来酰亚胺的N上,得到具有高量子产率的绿色荧光材料——N-苄基-3,4-二苯基马来酰亚胺(BDPM).采用各种分析方法分别对BDPM的结构和性能进行了表征,研究发现苄基的引入对材料量子产率的提高有重要的影响.
A herringbone structured compound, 3,4-bisthienylmaleimide (BTM), with reversible four-color and on/off switching upon external stimuli is reported here. Three kinds of BTM crystals with strong red (RC), orange (OC) and yellow (YC) fluorescence, as well as a brown solid (BS) with weak orange luminescence are obtained in the experiments. Heating, solvent vapor and pressure, including crushing and grinding, can reversibly switch BTM's emission between RC, OC, YC and BS. Base vapor (NEt3)-heating cycle treatment of BTM film in polystyrene can induce emission switching between bright/dark (on/off) states. The results of crystal structural analysis and photophysical property studies demonstrate that although OC and YC have the same crystal structure, they exhibit different fluorescent properties, due to their different surface structures. Heat induces metastable RC, with orderly pi-stacking, to turn into stable OC or YC, with brick stone stacking. Crushing can damage the surface structure of OC and transform it into YC without altering the crystal structure. Grinding OC or YC destroys the orderly stacking to yield amorphous BS.
The invention relates to a method for preparing a multiple-stimulation respond material by virtue of a two-step process. The method comprises the following steps: putting maleimide into a reaction bottle, adding N,N-dimethylformamide and a halogenating reagent, heating until the temperature reaches 58 DEG C for reacting for 48-72 hours, and adding water and dichloromethane sequentially for suction filtration to obtain 3,4-dihalogenmaleimide; putting 3,4-dihalogenmaleimide and a palladium bis(triphenylphosphine) dichloride catalyst into a flask, vacuumizing, then filling the flask with nitrogen, injecting anhydrous N,N-dimethylformamide and 2-(tributylstannyl)thiophene, increasing the temperature to 100 DEG C for reacting for 12 hours, cooling, then adding the mixed solution of dichloromethane and saturated potassium fluoride aqueous solution, then extracting, drying, filtering and purifying through column chromatography to obtain 3,4-bis(2'-thienyl)maleimide. The material prepared by the method provided by the invention has the advantages of good heat stability, simple synthesis steps, high solid-state fluorescent quantum efficiency and the like, and also has the properties of piezallochromy, thermochromism, solvent induced chromism and the like.