115198-11-3Relevant academic research and scientific papers
Sonogashira reactions for the synthesis of polarized pentacene derivatives
Schweizer, Stéphane,Erbland, Guillaume,Bisseret, Philippe,Lalevee, Jacques,Le Nouen, Didier,Blanchard, Nicolas
, p. 1180 - 1189 (2015)
Five dissymmetrically functionalized anthracene analogues (3a-e) were synthesized from commercially available 9,10-dibromoanthracene through an efficient bromine-iodine exchange followed by two successive Sonogashira coupling reactions. The resulting TMS-
Phenyleneanthracene derivatives as triplet energy acceptor/emitter in red light excitable triplet-triplet-annihilation upconversion
Zhong, Fangfang,Zhao, Jianzhang
, p. 909 - 918 (2016/10/09)
A series of anthracene derivatives with 9,10-substituents were prepared as triplet acceptors/emitters for triplet-triplet-annihilation (TTA) upconversion. Different linkages of C[sbnd]C single bonds and C[tbnd]C triple bonds were used to tune the singlet and triplet state energy levels, which may enhance the TTA upconversion. The study of the photophysical properties of the compounds indicates that the C[sbnd]C linker does not alter the T1 state energy level substantially, whereas the C[tbnd]C linker significantly reduced the T1 state energy levels. With nanosecond transient absorption spectroscopy, the intermolecular triplet-triplet-energy-transfer (TTET) process was studied. The lack of the upconversion for some anthracene derivatives was attributed to the inappropriate T1 energy levels thus the lack of TTET. On the other hand, different upconversion quantum yields were observed for some acceptors, although the TTET processes are similar. This result is due to the different TTA. These studies will be useful for future development of the TTA upconversion and for study of the triplet state properties of organic chromophores.
Efficient synthesis of 9,10-bis(phenylethynyl)anthracene derivatives by integration of sonogashira coupling and double-elimination reactions
Toyota, Shinji,Mamiya, Daiki,Yoshida, Rie,Tanaka, Ryo,Iwanaga, Tetsuo,Orita, Akihiro,Otera, Junzo
, p. 1060 - 1068 (2013/05/21)
9,10-Bis(phenylethynyl)anthracene (BPEA) derivatives were synthesized from 10-bromo-9-anthracenecarbaldehyde by stepwise Sonogashira coupling with phenylethynes and the one-shot double-elimination reaction with benzyl phenyl sulfones. Those two reactions could be integrated in a one-pot process to give unsymmetrically substituted BPEA derivatives in good yields by simple operations. This integrated process was applied to the synthesis of an extended BPEA derivative having an extra phenylethynyl group. The photophysical properties of the BPEA derivatives were investigated by UV/Vis and fluorescence spectroscopy. Georg Thieme Verlag Stuttgart · New York.
De novo design for functional amorphous materials: Synthesis and thermal and light-emitting properties of Twisted anthracene-functionalized bimesitylenes
Moorthy, Jarugu Narasimha,Venkatakrishnan, Parthasarathy,Natarajan, Palani,Huang, Duo-Fong,Chow, Tahsin J.
supporting information; scheme or table, p. 17320 - 17333 (2009/07/11)
The unique structural attributes inherent to D2dsymmetric rigid tetraarylbimesityls render their close packing in the solid state difficult. We have exploited the indisposed tendency of such modules based on the bimesityl scaffold toward crystallization to design a novel class of amorphous functional materials with high glass transition temperatures and thermal stability (T d > 400 °C). It is shown that a variety of 2- and 4-fold anthracene-functionalized bimesityls, 1-7, that exhibit excellent amorphous properties (Tg = ca. 190-330 °C) can be readily prepared via facile Pd(0)-mediated cross-coupling strategies. As the communication between the bimesityl core and the anchored anthracenes is negligible or only marginal, the trends observed for luminescence of model constituent anthracenes are reproduced in the condensed- phase photoluminescence and electroluminescence of 1-7. In other words, the emission characteristics, i.e., λmax and quantum yields, are readily modulated via appropriate modification of the fluorophores. The functional behavior of this unique class of amorphous materials based on the bimesityl scaffold is demonstrated by fabrication of OLED devices. The 2-fold functionalized derivatives 1 and 2 lend themselves to sublimation techniques, so that the electroluminescence is captured with high efficiencies at low turn-on voltages (3.5-6.5 V). The device ITO/NPB (400 A)/1% 2:MADN (400 A)/TPBI (400 A)/LiF (10 A)/AI (1500 A) for 2 yields the highest luminance of ～13 900 cd/m2 at 17.5 V, a maximum luminance efficiency of ～7.4 cd/A at 4.5 V, and a power efficiency of ～5.3 Im/W at 4.0 V. Further, at a brightness of 800 cd/m 2 and a current density of 13.8 mA/cm2, the device is found to exhibit excellent luminance efficiency of 5.8 cd/A, external quantum efficiency of 4.3% with a power efficiency of 2.2 Im/W, and pure blue light with a CIExy (x= 0.13, y= 0.18). The performance characteristics of the devices fabricated for 1 and 2 are remarkable. Although the 4-fold functionalized systems did not permit sublimation leading to spin-coating as a means for device fabrication, the observed electroluminescence for 4 and 5 attests to a broader scope and applicability of this new category of amorphous molecules for application in OLEDs.
Conjugation enhancement of intramolecular exciton migration in poly(p-phenylene ethynylene)s
Nesterov, Evgueni E.,Zhu, Zhengguo,Swager, Timothy M.
, p. 10083 - 10088 (2007/10/03)
Efficient energy migration in conjugated polymers is critical to their performance in photovoltaic, display, and sensor devices. The ability to precisely control the polymer conformation is a key issue for the experimental investigations and deeper unders
Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution
Swager, Timothy M.,Gil, Caroline J.,Wrighton, Mark S.
, p. 4886 - 4893 (2007/10/02)
The poly(p-phenyleneethynylene) molecules, PI-PIII, synthesized by a palladium-catalyzed cross-coupling reaction of diiodobenzene derivatives and derivatives of 1,4-diethynylbenzene, are highly luminescent materials.The polymers are soluble by virtue of the -OC16H33 groups introduced on the aromatic rings and by controlling their molecular weight.The fluorescent quantum yields are between 0.35 and 0.40 depending on the material.The excited-state lifetimes of the polymers are 1-2 ns, slightly shorter than that of the model compund, 1,4-diphenylethynyl-2,5-dibutoxybenzene, which has a lifetime of 3 ns.Incorporation of anthracene, coupled at the 9,10-positions by using 9,10-dibromoanthracene, into the polymer backbone decreases the quantum yield to between 0.05 and 0.27 depending on the anthracene content.In addition, low-energy electronic transitions and longer wavelength emission bands associated with the anthracene group are produced.The polymers harvest optical energy and transfer it to the anthracene resulting in emission from this chromophore.In the case where only terminal anthracene units, introduced by using 9-bromo-10-phenylethynylanthracene, are present, the process is very efficient with >95percent of the energy being transferred to the end groups.
