291753-68-9Relevant academic research and scientific papers
Molecular design of benzothienobenzothiophene-cored columnar mesogens: Facile synthesis, mesomorphism, and charge carrier mobility
Liu, Chun-Xia,Wang, Hu,Du, Jun-Qi,Zhao, Ke-Qing,Hu, Ping,Wang, Bi-Qin,Monobe, Hirosato,Heinrich, Beno?t,Donnio, Bertrand
supporting information, p. 4471 - 4478 (2018/05/04)
Benzothienobenzothiophene (BTBT) liquid-crystalline semiconductors are arousing a lot of interest due to their long-range ordered, self-organizational abilities and high-charge carrier transport properties. In this work, we report the design and the straightforward synthesis of a homologous series of compounds containing the BTBT substructure by the successive Suzuki cross-coupling and FeCl3 oxidative Scholl cyclodehydrogenation reaction. Target π-conjugated aromatic, H-shaped sanidic mesogens self-organize into a classical hexagonal columnar mesophase over wide temperature ranges as deduced from polarized optical microscopy (POM), differential scanning calorimetry (DSC), and small-angle X-ray scattering (SAXS) investigations. UV/Vis absorption and photoluminescence spectra, measured in both solution and films, revealed strong photoluminescence with high quantum yields. The charge carrier mobility measured by the time-of-flight (TOF) technique showed a balanced ambipolar hole and electron mobility in the range of 10-3 cm2 V-1 s-1 between 100 and 230 °C in the mesophase. These BTBT-based columnar liquid crystals may represent attractive candidates to be incorporated within one-dimensional organic optoelectronic devices.
Facile bottom-up synthesis of coronene-based 3-fold symmetrical and highly substituted nanographenes from simple aromatics
Zhang, Qiang,Peng, Hanqing,Zhang, Guishan,Lu, Qiongqiong,Chang, Jian,Dong, Yeye,Shi, Xianying,Wei, Junfa
supporting information, p. 5057 - 5064 (2014/04/17)
A facile and efficient self-sorting assemble (CSA) strategy has been paved for bottom-up construction of the 3-fold symmetrical and highly substituted hexa-cata-hexabenzocoronenes (c-HBCs), the trithieno analogues, and larger disc-shaped PAHs from simple
Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: The effect of heteroatom and substitution pattern on phase stability
Sienkowska, Monika J.,Farrar, John M.,Zhang, Fan,Kusuma, Sharat,Heiney, Paul A.,Kaszynski, Piotr
, p. 1399 - 1411 (2008/02/07)
A series of closely related tetrasubstituted derivatives of benzo[c]cinnoline (1), tetraazapyrene (2), phenanthrene (3), and pyrene (4) were investigated for their mesogenic properties using thermal, optical, spectroscopic, and powder XRD analyses. Only three 3,4-dioctyloxyphenyl derivatives exhibited mesogenic properties. Substitution of N for CH (3 → 1 and 4 → 2 pairs) and also increase of the core element size (1 → 2 and 3 → 4 pairs) significantly increases the mesophase stability. The findings and observed trends were rationalized by analysis of conformational properties which included calculation of the planarization energy, and modeling of aliphatic chain density and fill fractions. MO calculations showed that the tetraaza derivative 2c is significantly electron deficient and suitable for electron conductive materials. The Royal Society of Chemistry.
Self-assembled fluorescent hexaazatriphenylenes that act as a light-harvesting antenna
Ishi-I, Tsutomu,Murakami, Koh-Ichi,Imai, Yusuke,Mataka, Shuntaro
, p. 5752 - 5760 (2007/10/03)
In this paper we report the self-assembling nature of fluorescent hexaazatriphenylenes (HATs) 6a-d with six alkyl/alkoxy-chain-containing biphenyl groups and their application to light-harvesting antennae. In a nonpolar solvent and the film state, the HAT
Synthesis and mesogenic properties of novel board-like liquid crystals
Artal,Toyne,Goodby,Barbera,Photinos
, p. 2801 - 2807 (2007/10/03)
The syntheses of novel octa- and tetra-substituted systems based on tetrabenz[a,c,h,j]anthracene are reported. The disc-shaped octa-substituted material exhibits a columnar mesophase, whereas the tetra-substituted material exhibits a lamellar phase. Binar
Extended triphenylenes: Synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)triphenylenes and dodeca(alkoxy) tris(triphenylenylene)s
Yatabe, Tetsuo,Harbison, Martha A.,Brand, Johann Diedrich,Wagner, Manfred,Muellen, Klaus,Samori, Paolo,Rabe, Juergen P.
, p. 1519 - 1525 (2007/10/03)
Palladium-catalyzed cross-coupling between 3,4-dialkoxyphenylboronic acids (1a-d) and 2,3,6,7,10,11-hexabromotriphenylene (2) provided 2,3,6,7,10,11-hexakis[3,4-bis(alkoxy)phenyl]triphenylenes, C18H6[C6H3(OC(n)H(2n + 1)2]6 where n = 6, 8, 10, and 12 (3a-d). Cyclodehydrogenation of the aryl-substituted triphenylenes 3a-d using ferric chloride oxidation followed by methanol reduction produced 6,6',6'',7,7',7'',10,10',10'',11,11',11''-dodecaalkoxy-2,3':3,2':2',3''- tris(triphenylenylene)s, C54H18(OC(n)H(2n + 1))12 where n = 6, 8, 10, and 12 (4a-d). The mesomorphic properties of the compounds 3a-d and 4a-d were investigated by differential scanning calorimetry (DSC) measurements, polarizing microscopy, and wide angle X-ray diffraction (WAXD). The triphenylenes 3a-d exhibited a columnar mesophase in the range of 111-126, 85-104, 74-103, and 47-101 °C, respectively. Upon oxidation of the moiety, the columnar mesophases shift to higher temperatures and exist in a much broader range of temperatures: for the tris(triphenylenylene)s 4a-d, they have been observed in the range of 180-430, 150-370, 120-322, and 104-306 °C, respectively. Finally, the self-assembly at the interface between a solution of 4c and a graphite substrate has been studied by scanning tunneling microscopy. Molecularly resolved imaging revealed a highly ordered monolayer exhibiting a two-dimensional hexagonal lattice.
