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• 1010685-23-0 C₃₅H₅₆BrNO₂ 
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Relevant academic research and scientific papers

Molecular design of benzothienobenzothiophene-cored columnar mesogens: Facile synthesis, mesomorphism, and charge carrier mobility

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

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

Columnar mesomorphism of fluorescent board-shaped quinoxalinophenanthrophenazine derivatives with donor-acceptor structure

Quinoxalino[2′,3′:9,10]phenanthro[4,5-abc]phenazine (QPP) dyes have been studied as electron acceptor materials, fluorophores, and building blocks for self-organizing organic semiconductors. Condensation of tetraketopyrene with electron-rich diamino-terphenylene and -triphenylene derivatives generates new donor-acceptor QPP derivatives that display columnar mesomorphism over wide ranges of temperature; are fluorescent in solution, liquid crystal, and solid phases; and have electron acceptor properties. Also reported are the synthesis and properties of the first diamino-(tetraalkoxy) triphenylene as a valuable new synthon.

Columnar mesophases from half-discoid platinum cyclometalated metallomesogens

A series of liquid crystals have been synthesized and studied based upon mononuclear ortho-platinated rod-like heteroaromatic and 1,3-diketonate ligands. The liquid crystalline properties of these molecules were investigated using polarized light optical

Extended triphenylenes: Synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)triphenylenes and dodeca(alkoxy) tris(triphenylenylene)s

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.