288105-04-4Relevant articles and documents
Synthesis of Fluorene-Bridged Arylene Vinylene Fluorophores: Effects of End-Capping Groups on the Optical Properties, Aggregation Induced Emission
Zhang, Guo-Feng,Chen, Tao,Chen, Ze-Qiang,Aldred, Matthew P.,Meng, Xianggao,Zhu, Ming-Qiang
, p. 939 - 947 (2015/09/01)
We have synthesized a series of fluorene-based fluorophores, in which a central fluorene core has been modified with different peripheral arylene vinylene substituents that are able to activate aggregation-induced emission (AIE) characteristics. 9,9-Dioctylfluorene doubly end-capped at the 2,7-positions with triphenylethene groups, such as 4-(2,2-diphenylvinyl)phenyl (F1-(2,2)-HTPE) and 4-(1,2-diphenylvinyl)phenyl (F1-(1,2)-HTPE) were synthesized and compared to the tetraphenylethene analogue (F1-TPE). Both F1-(2,2)-HTPE and F1-(1,2)-HTPE glow with a deep blue fluorescence in THF solution with emission maxima (λem) of 426 and 403 nm, respectively. The λem slightly red-shifts in the solid-state to 458 nm for F1-(2,2)-HTPE and 437 nm for F1-(1,2)-HTPE. The fluorescence quantum yields (Φ;F) of F1-(2,2)-HTPE (?F=35.1 %) and F1-(1,2)-HTPE (?F=26.2%) were found to be higher in solution compared to the near quenching of F1-TPE (?F=0.1%). Consequently, this results in weaker AIE-stability of F1-(2,2)-HTPE (αAIE=1.5) and F1-(1,2)-HTPE (αAIE=1.9) compared to F1-TPE (αAIE=125), suggesting that four phenyl groups are necessary for efficient AIE-activity of these fluorene bridged arylene vinylene type materials. In addition, decreasing the steric hindrance around the arylene vinylene moiety by removal of a phenyl ring is another method to decrease the AIE characteristics, in a similar manner to the commonly known ?phenyl-locking?. Non-polar triphenylethenes are poorer AIE materials than their tetraphenylethene analogues. Replacing the hydrogen atom of F1-(2,2)-HTPE with a cyano group affords fluorene end-capped with 2,3,3-triphenylacrylonitrile (F1-TPAN), which boosts the AIE-effect to αAIE=90.5 and red-shifts the solid-state emission (λem=528 nm) with near quenching in THF solution (?F=0.12%). X-ray crystallographic analysis of F1-TPAN indicates that the introduction of cyano groups can not only diminish the intramolecular steric hindrance in comparison of F1-TPE, but also improve the molecular cohesion ability via multiple C-H···N interactions. Four different arylene vinylene substituents attached to the fluorene were synthesized, and the disparities of AIE-effect of these compounds were discussed. The cyano-groups in F1-TPAN will not only reduce the steric congestion of the peripheral phenyl rings, but also appreciably improve the molecular cohesion ability via multiple C-H?N interactions.
Synthesis and aggregation-induced emission properties of tetraphenylethylene-based oligomers containing triphenylethylene moiety
Jana, Debabrata,Ghorai, Binay K.
, p. 6838 - 6842 (2013/01/15)
Three new tetraphenylethylene based oligomers bearing triphenylethylene moiety were synthesized utilizing Suzuki coupling reaction and their aggregation-induced emission properties were studied. They show excellent solubility in common organic solvents and emit light in blue region (440-504 nm). AIE effect is predominant for tetra-substituted TPE (20.1-fold) than mono-substituted one (4.5-fold).
Suppression of aggregation-induced fluorescence quenching in pyrene derivatives: Photophysical properties and crystal structures
Liang, Zuo-Qin,Li, Ye-Xin,Yang, Jia-Xiang,Ren, Yan,Tao, Xu-Tang
, p. 1329 - 1333 (2011/04/15)
Two new pyrene-based fluorophores, namely 1-[4-(2,2-diphenylvinyl)phenyl] pyrene (PVPP) and 1,3,6,8-tetrakis[4-(2,2-diphenylvinyl)phenyl]pyrene (TPVPP), were synthesized through Suzuki coupling reaction and well characterized. PVPP successfully suppresses the fluorescence quenching of pyrene units in the solid state, displaying aggregation-induced enhanced emission. Despite the same substituent, TPVPP shows a different fluorescent behavior. On the basis of the crystal structures, the distinct optical behavior is discussed and clarified. The intermolecular C-H?π interaction has a dramatic effect on their photophysical properties in the solid state.
Efficient and stable dye-sensitized solar cells based on phenothiazine sensitizers with thiophene units
Wu, Wenjun,Yang, Jiabao,Hua, Jianli,Tang, Jin,Zhang, Lei,Long, Yitao,Tian, He
supporting information; experimental part, p. 1772 - 1779 (2010/08/19)
Three new phenothiazine organic dyes containing thiophene, 3-(5-(3-(4-(bis(4-methoxy phenyl)amino)phenyl)-10-octyl-10H-phenothiazin-7-yl) thiophen-2-yl)-2-cyanoacrylic acid (P1), 3-(5-(3-(4-(diphenylamino)phenyl)-10- octyl-10H-phenothiazin-7-yl)thiophen-2-yl)-2-cyanoacrylic acid (P2) and 2-cyano-3-(5-(10-octyl-3-(4-(2,2-diphenylvinyl)phenyl)-10H-phenothiazin-7-yl) thiophen-2-yl) acrylic acid (P3) were designed and synthesized as sensitizers for application in dye-sensitized solar cells (DSSCs). For these dyes, the phenothiazine derivative moiety and the cyanoacetic acid take the roles of electron donor and electron acceptor, respectively. The absorption spectra, electrochemical and photovoltaic properties of P1-P3 and the cell long-term stability were extensively investigated. It was found that HOMO and LUMO energy level tuning can be conveniently accomplished by alternating the donor moiety. The DSSCs based on dye P2 showed the best photovoltaic performance: a maximum monochromatic incident photon-to-current conversion efficiency (IPCE) of 84.9%, a short-circuit photocurrent density (Jsc) of 10.84 mA cm -2, an open-circuit photovoltage (Voc) of 592 mV, and a fill factor (ff) of 0.69, corresponding to an overall conversion efficiency of 4.41% under standard global AM 1.5 solar light conditions. These results demonstrated that the DSSCs based on phenothiazine dyes could achieve both high performance and good stability.
NOVEL THIOPHENE-BASED DYE AND PREPARATION THEREOF
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Page/Page column 70-72, (2009/05/28)
The present invention relates to a thiophene-based dye and a preparation thereof, and more particularly, to dye compounds, which are used for a dye-sensitized solar cell (DSSC), and provides better molar extinction coefficient, JSc (short-circuit photocurrent density) and photoelectric conversion efficiency than a conventional dye to enhance efficiency of a solar cell.
A new type of light-emitting naphtho[2,3-c][1,2,5]thiadiazole derivatives: Synthesis, photophysical characterization and transporting properties
Wei, Peng,Duan, Lian,Zhang, Deqiang,Qiao, Juan,Wang, Liduo,Wang, Ruji,Dong, Guifang,Qiu, Yong
body text, p. 806 - 818 (2009/04/21)
We report a new series of naphtho[2,3-c][1,2,5]thiadiazole (NTD) derivatives which present both carrier transporting property and high fluorescence quantum yield. Optical absorption and emission property, film morphology and thermal stability of these com
Synthesis, morphology, and optical properties of tetrahedral oligo(phenylenevinylene) materials
Wang, Shujun,Oldham Jr., Warren J.,Hudack Jr., Raymond A.,Bazan, Guillermo C.
, p. 5695 - 5709 (2007/10/03)
A novel topological strategy is described for designing amorphous molecular solids suitable for optoelectronic applications. In this approach, chromophores are attached to a tetrahedral point of convergence. Stilbenoid units were covalently linked to tetraphenylmethane, tetraphenyladamantane, or tetraphenylsilane cores using palladium catalyzed coupling methodology. Thus, reaction of E(C6H5X)4 (E = C and adamantane, X = I; E = Si, X = Br) with styrene or 4,4'-tert-butylvinylstilbene under Heck coupling conditions yields the corresponding tetrakis(stilbenyl) (E(STB)4) and tetrakis(4-tert- butylstyrylstilbenyl) (E((t)BuSSB)4) compounds. Similarly, reaction of 1,1- diphenyl-2-(4-dihydroxyboronphenyl)ethene or 2-(4-pinacolatoboronphenyl)-3,3- diphenylacrylonitrile with tetrakis(4-bromophenyl)methane using Suzuki coupling methodology gives tetrakis(4,4'-(2,2-diphenyl-vinyl)-1, 1'- biphenyl)methane (C(DPVBi)4) or tetrakis(4,4'-(3,3-diphenylacrylonitrile)- 1,1'-biphenyl)methane (C(DPAB)4), respectively, in good yields. Compounds with more extended conjugation can also be prepared. Thus, reaction of excess 1-(4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene with C(C6H4I)4 provides tetrakis(4-(4'-(4''-tert-butylstyryl)styryl)stilbenyl)methane (C(4R-(t)Bu)4) in low yield (~20%). The more soluble analogue, tetrakis(4-(4'-(3,5-di- tert-butylstyryl)styryl)stilbenyl)methane (C(4R-2(t)Bu)4) is prepared similarly using 1-(3',5'-di-tert-butylstyryl)-4-(4'-vinylstyryl)benzene and in better yield (~80%). Alkoxy substituents can also be used to increase solubility. Tetrakis((4-(2',5'-dioctyloxy-4'-styryl)styryl)stilbenyl)methane, C(4R-(OC8H17)2)4, was prepared by treatment of C(C6H4I)4 with excess 2,5-dioctyloxy-1-styryl-4(4'-vinylstyryl)benzene (yield ~73%). The simple stilbenyl-derivatives were found by DSC measurements and powder diffraction experiments to be crystalline compounds. Comparison of single-crystal X-ray diffraction data shows that C(STB)4 and Si(STB)4 form isomorphous crystals. The larger E((t)BuSSB)4, C(DPVBi)4, and C(DPAB)4 compounds readily form amorphous glasses with elevated glass transition temperatures (T(g) = 142190 °C) in the absence of solvent. Extending the conjugation length of the arm leads to more stable glasses. For example, the glass transition temperature of C(4R-(t)Bu)4 was measured at 230 °C. Solution phase optical spectroscopic data of E((t)BuSSB)4 (E = C, adamantane, and Si) are characteristic of the parent distyrylbenzene chromophore. Films, however, show broad and significantly red-shifted emission spectra. In contrast, C(DPVBi)4 gives absorption and emission spectra which are nearly identical between dilute solution phase samples and neat solid films. The emission of C(DPAB)4 is broad and structureless, reminiscent of exciplex or excimer emission. Films of the tetramers with longer arms (C(4R-(t)Bu)4, C(4R- 2(t)Bu)4, and C(4R-(OC8H17)2)4) show emission properties which are dependent on sample history. Annealing the sample at elevated temperature leads to red-shifted emission as a result of better interdigitation between the optically active fragments.
