- Extended phenylene based microporous organic polymers with selective carbon dioxide adsorption
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Two microporous conjugated polymers with extended phenylene backbones have been synthesized through Suzuki cross-coupling reactions. The structure and the pores of the polymers have been controlled by the use of para- and meta-structure directing 1,3,5-triphenyl tribromide monomers. Gas sorption studies revealed an unprecedented CO2 selectivity over N2 for these conjugated polymer networks. The networks have furthermore been tested as hydrogen storage materials and showed significant hydrogen uptake at high pressures.
- Rao, K. Venkata,Mohapatra, Sudip,Kulkarni, Chidambar,Maji, Tapas Kumar,George, Subi J.
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- Solvent-dependent metal-free chemoselective synthesis of benzimidazoles and 1,3,5-triarylbenzenes from 2-amino anilines and aryl alkyl ketones catalyzed by I2
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A solvent-dependent I2-catalyzed chemoselective reaction was developed for the synthesis of benzimidazoles and 1,3,5-triarylbenzenes via the annulation of 2-amino anilines and aryl alkyl ketones or the cyclization of aryl alkyl ketones, respectively. With 1,4-dioxane as the solvent, sequential C[sbnd]N bond formation followed by C(CO)-C(CH3) bond cleavage leads to the formation of benzimidazoles in a highly selective manner while aldol-type self-condensation of aryl alkyl ketones predominates using PhNO2 or PhCl as the solvent to afford 1,3,5-triarylbenzenes.
- Ding, Yuxin,Ma, Renchao,Ma, Yongmin
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supporting information
(2021/04/09)
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- Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes
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Herein we report a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)2 complex in situ generated from NiCl2·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established.
- Yang, Kai,Wang, Pengfei,Sun, Ze-Ying,Guo, Minjie,Zhao, Wentao,Tang, Xiangyang,Wang, Guangwei
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supporting information
p. 3933 - 3938
(2021/05/26)
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- Condensation of 2-methylindole with acetophenones: An unexpected formation of 2-arylanilines
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2-Methylindole condenses with acetophenones under acidic conditions to produce 2-arylanilines in moderate to good yields. The reaction proceeds well with a range of 3′- and 4′- substituted acetophenones (fluoro-, chloro-, bromo-, iodo-, methyl, methoxy),
- Noland, Wayland E.,Novikov, Alexei V.,Brown, Christopher D.
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supporting information
p. 3442 - 3452
(2019/11/03)
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- DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions
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A facile method for the synthesis of 1,3,5-triarylbenzenes is developed via cyclotrimerization of acetophenones in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as an efficient Bronsted acid catalyst under solvent-free conditions. This synthetic pr
- Prasad, Davinder,Preetam, Amreeta,Nath, Mahendra
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p. 252 - 256
(2013/05/08)
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- Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: Straightforward access to 1,3,5-triarylbenzenes under mild conditions
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An efficient triple condensation reaction of aryl methyl ketones catalyzed by ethylenediamine and trifluoroacetic acid was reported. A broad scope of 1,3,5-triarylbenzenes was obtained in good to excellent yields. The reaction provides a novel and practical approach to access organic materials of polycyclic aromatic hydrocarbons under mild conditions.
- Zhang, Shao-Liang,Xue, Zhao-Feng,Gao, Ya-Ru,Mao, Shuai,Wang, Yong-Qiang
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supporting information; experimental part
p. 2436 - 2439
(2012/06/01)
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- Synthesis and structural analysis of some podands with C 3 symmetry
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The multistep syntheses of C3-symmetrical tripodands with terminal triple bonds or azide groups exhibiting 1,3,5-triarylbenzene and 2,4,6-triaryl-1,3,5-triazine cores are reported herein. The structures of the newly synthesized compounds are su
- Woiczechowski-Pop, Adrian,Dobra, Ioana L.,Roiban, Gheorghe D.,Terec, Anamaria,Grosu, Ion
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p. 3579 - 3588
(2012/11/07)
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- Three-carbazole-armed host materials with various cores for RGB phosphorescent organic light-emitting diodes
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A series of three-carbazole-armed host materials containing various arylene cores, like benzene (1,3,5-tris(3-(carbazol-9-yl)phenyl)-benzene, TCPB), pyridine (2,4,6-tris(3-(carbazol-9-yl)phenyl)-pyridine, TCPY), and pyrimidine (2,4,6-tris(3-(carbazol-9-yl)phenyl)-pyrimidine, TCPM), were developed for red, green, and blue phosphorescent organic light-emitting diodes (OLEDs). An intramolecular charge transfer was observed for TCPY and TCPM with heterocyclic cores of pyridine and pyrimidine, giving bathochromic shifts in the photoluminescent spectrum and reduced energy band gaps in comparison with TCPB with a benzene core. In addition, lower energy singlet and triplet excited states, reduced lowest unoccupied molecular orbital (LUMO) energy level, smaller singlet-triplet exchange energy (ΔEST), and improved bipolarity were also achieved with introducing heterocycles of pyridine and pyrimidine instead of benzene. In contrast to the slightly decreased triplet energy (ET), a significantly decreased ΔEST was achieved by introducing heterocycles of pyridine and pyrimidine as the core, and the more nitrogen atoms in the central heterocycle, the smaller ΔE ST is achieved. Reduced driving voltages were achieved for the green and red phosphorescent OLEDs by utilizing TCPY and TCPM as the host due to their decreased ΔEST and lower-lying LUMO energy level, proving that more carriers must be injected into the emitting layer through the host molecules rather than direct carrier trapping by the dopant. Moreover, improved efficiency and suppressed efficiency roll-off were also achieved for the green and red phosphorescent OLEDs based on TCPY and TCPM due to their improved bipolarity and thus improved carrier balance.
- Su, Shi-Jian,Cai, Chao,Kido, Junji
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scheme or table
p. 3447 - 3456
(2012/06/04)
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- Multifunctional electron-transporting indolizine derivatives for highly efficient blue fluorescence, orange phosphorescence host and two-color based white OLEDs
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In this work, derivatives of indolizine are first used as electron-transporting host materials for hybrid fluorescence/phosphorescence white organic light-emitting devices (F/P-WOLED). Of the indolizine derivatives, a blue fluorescent material BPPI (3-(4,4′-biphenyl)-2-diphenylindolizine) was found to have: (1) blue emission with high quantum yields, (2) good morphological and thermal stabilities, (3) electron-transporting properties, and (4) a sufficiently high triplet energy level to act as a host for red or yellow-orange phosphorescent dopants. The multifunctional BPPI enables adaptation of several simplified device configurations. For example, a non-doped blue fluorescent device exhibits good performance with an external quantum efficiency of 3.16% and Commission Internationale de l'Eclairage coordinates of (0.15, 0.07). A high-performance orange phosphorescent device was found to have a high current efficiency of 23.9 cd A-1. Using BPPI, we also demonstrate a F/P-WOLED with a simplified structure, stable emissions and respectable performance (current and external quantum efficiencies of 17.8 cd A-1 and 10.7%, respectively).
- Wan, Jing,Zheng, Cai-Jun,Fung, Man-Keung,Liu, Xiao-Ke,Lee, Chun-Sing,Zhang, Xiao-Hong
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experimental part
p. 4502 - 4510
(2012/08/08)
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- Simple and convenient synthesis of 1,3,5-triarylbenzenes from ketones
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A new and efficient synthesis of a series of 1,3,5-triarylbenzenes was accomplished in good yields via the triple condensation of aryl methyl ketones promoted by thionyl chloride in anhydrous ethanol. The method is simple and convenient.
- Hu, Anan,Zhang, Anjiang,Ding, Lisheng,Lei, Xinxiang,Zhang, Lixue
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p. 720 - 721
(2008/09/20)
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- Pentamacrocyclic Tris Crown Hosts. - Selective Binding of Cationic, Anionic, and Neutral Guest Compounds
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The tris-crown host compounds 1-4 were synthesized for the first time.The X-ray structures of 2 and the 1:3 complex of 1 and KSCN were determined.Whereas in the free crown 2 a less well preorganized molecular cavity is encountered, in the complex of 1 wit
- Wallon, Alexander,Werner, Ute,Mueller, Walter M.,Nieger, Martin,Voegtle, Fritz
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p. 859 - 867
(2007/10/02)
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- New Trigonal Lattice Hosts: Stoicheiometric Crystal Inclusions of Laterally Trisubstituted Benzenes - X-Ray Crystal Structure of 1,3,5-Tris-(4-carboxyphenyl)benzene*Dimethylformamide
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New host molecules with a central 1,3,5-trisubstituted benzene ring and rigidly attached lateral arms composed of aryl or arylethynyl and extra fuctional groups are reported.They are shown to give more than thirty clathrates with a wide variety of organic solvents comprising alicyclic, aromatic, heterocyclic, dipolar aprotic, and protic molecules.Inclusion selectivities and stoicheiometries of the different clathrates are discussed.The crystal structure of (2a)*dimethylformamide (DMF) (1:3) inclusion compound has been determined from single-crystal X-ray diffraction.The crystals show R3 symmetry.There are six host and eighteen guest molecules in the hexagonal unit cell with a=b=23.160(9) and c=11.812(3) Angstroem.The final linear R is 0.082 for 1518 unique reflections.The host molecule adopts a propeller conformation with perfect three-fold symmetry and acts as a donor in hydrogen bonds to three DMF molecules.In the crystal structure the host-guest units are arranged stack-wise.
- Weber, Edwin,Hecker, Manfred,Koepp, Erich,Orlia, Wolfgang,Czugler, Matyas,Csoeregh, Ingeborg
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p. 1251 - 1258
(2007/10/02)
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