34380-89-7Relevant academic research and scientific papers
Mesogenic heterocycles derived from quinoxaline Schiff Bases
Kuo, Hsiu-Ming,Ko, Wan-Ping,Hsu, Yu-Te,Lee, Gene-Hsiang,Lai, Chung K.
, p. 6321 - 6333 (2016)
Three new series of heterocyclic quinoxaline Schiff Bases 1–2 were prepared, characterized and their mesomorphic properties were investigated. These compounds 1 and 2 are in fact geometric isomers in which an imine moiety (e.g., [sbnd]C[dbnd]N) is inversely incorporated into quinoxaline, leading to an opposite local dipole. Two single crystallographic structures 1 (m=8, n=8) and 2a (m=12, n=8) were determined by X-ray crystallographic analysis in order to understand the effect of mesomorphic properties. Weak H-bonds, CH–π and π–π interactions were found in both crystals, which were attributed to the formation of mesomorphic behavior. Variable temperature FT-IR experiments were performed to confirm the induced H-bonds. All series?of compounds 1–2 exhibited N/SmC or SmC phases, which were identified by optical microscope and confirmed by powder X-ray diffraction experiments. Compounds 2a have a slightly wider range of mesophase temperatures than that of compounds 1 and 2b.
Polarization effect in luminescent mesogenic BF2 complexes derived from heterocyclic benzothiazoles
Hsu, Yuan?Chun,Wang, Chun?Yang,Hsiao, Pei?Chi,Cai, Yi-Hong,Lee, Gene?Hsiang,Lai, Chung K.
, (2019/12/09)
Two series of benzo(thia)xazoles 1–2 and one series of boron difluoride complexes 2-BF2 derived from benzothiazoles 2 were reported, and their mesomorphic and optical properties were investigated. The crystal and molecular structures of compound 2 and 2-BF2 (all n = 8) were determined by means of X?ray structural analysis, and both crystallize in the triclinic P-1 and monoclinic P21/c. The geometry at boron center is perfectly tetrahedral, and the overall molecular shapes are considered as rod?shape. Both benzo(thia)xazoles 1 and 2 exhibited N or/and SmC phase, and boron complexes 2-BF2 formed N or/and SmC phase. Benzothiazoles 2 showed a much wider temperature range of mesophase than those of benzoxazoles 1, which were attributed to the better polarization by sulfur atom incorporated. Boron complexes 2-BF2 (n = 10, 12) emitted a yellow?to?green emission at λmax = 569–571 nm in CH2Cl2. This is the first mesogenic BF2 complexes derived from benzothiazoles.
Phthalocyanine-based discotic liquid crystals switching from a molten alkyl chain type to a flying-seed-like type
Nakamura, Hiromu,Sugiyama, Kouki,Ohta, Kazuchika,Yasutake, Mikio
, p. 7297 - 7306 (2017/08/03)
We have synthesised a series of phthalocyanine-based discotic liquid crystals, (m-CnOPhO)8PcCu (n = 1-20: 2a-o), and investigated their mesomorphism by using a polarizing optical microscope (POM), a differential scanning calorimeter (DSC) and a temperature-dependent small angle X-ray diffractometer. We found that each of the derivatives 2a-o shows mesomorphism. However, the mesomorphism of the (m-CnOPhO)8PcCu derivatives strongly depends on the alkoxy chain length (n). The mesomorphism of the short chain-substituted derivatives 2a-e for n = 1-5 is a flying-seed-like type induced by flip-flop of the peripheral bulky substituents, whereas the mesomorphism of the long chain-substituted derivatives 2j-o for n = 10-20 is a conventional molten alkyl chain type induced by melting of the long alkyl chains. The moderately long chain derivatives (2f-i) for n = 6-9 in between show both types of mesophases. The detailed temperature-dependent X-ray diffraction measurements were carried out for three representative derivatives, 2b (n = 2 for n = 1-5), 2h (n = 8 for n = 6-9), and 2o (n = 20 for n = 10-20). As a result, we revealed that the Colro(P2m) mesophase in 2b (n = 2) gave a halo denoted as Haloarom. at d ? 5.2 ? due to flip-flop of the bulky aromatic substituents, and that the Colho mesophase in 2o (n = 20) gave a halo denoted as Haloalkyl at d ? 4.6-4.8 ? due to melting of the long alkyl chains. Therefore, we can distinguish the type of mesophase from Haloarom. and Haloalkyl. Very interestingly, the (m-C8OPhO)8PcCu (2h) derivative having moderately long alkyl chains gave Haloalkyl at about 4.8 ? in the lower temperature mesophase of Colho, but Haloarom. at about 5.2 ? in the higher temperature mesophase of Colro(P21/a). This means that melting of the alkyl chains induces the Colho phase in the lower temperature region, but that flip-flop of the bulky aromatic substituents induces the Colro(P21/a) phase in the higher temperature region. This unusual reverse phase transition sequence from a higher symmetry of the Colh mesophase to a lower symmetry of the Colr mesophase on a heating stage is attributable to such a unique stepwise melting of these two different types of substituents. To the best of our knowledge, this mesogen (2h) is the first example switching mesomorphism from the molten alkyl chain type to the flying-seed-like type in a discotic liquid crystal.
Discotic liquid crystals of transition metal complexes 45?: Parity effect of the number of d-electrons on stacking distances in the columnar mesophases of octakis-(M-alkoxyphenoxy)phthalocyaninato metal(II) complexes
Sato, Hiroyuki,Igarashi, Kensaku,Yama, Yoshitaka,Ichihara, Masahiro,Itoh, Eiji,Ohta, Kazuchika
, p. 1148 - 1158 (2013/01/15)
We have synthesized 34 novel homologous discotic liquid crystals, octakis(m-alkoxyphenoxy)phthalocyaninato metal(II) {abbreviated as (m-C nOPhO)8PcM (M = Co(1), Ni(2), Cu(3), Zn(4) and H 2(5); n = 8(a), 10(b), 12(c), 14(d)
Columnar/smectic metallomesogens derived from heterocyclic benzoxazoles
Wu, I-Tzu,Chaing, Pei-Yi,Chang, Wen-Jung,Sheu, Hwo-Shuenn,Lee, Gene-Hsiang,Lai, Chung K.
scheme or table, p. 7358 - 7369 (2011/10/12)
The synthesis, mesomorphic behavior, and optical properties of two new series of metal complexes 1a,b-M (M=Pd, Cu, Zn) derived from benzoxazoles 2a,b are reported. The crystal and molecular structures of mesogenic 5-decyloxy-2-(6-decyloxybenzooxazol-2-yl)
2-(Dialkylamino)-4H-1-benzopyran-4-one derivatives modify chloride conductance in CFTR expressing cells
Mazzei, Mauro,Nieddu, Erika,Folli, Chiara,Caci, Emanuela,Galietta, Louis V.J.
, p. 961 - 970 (2007/10/03)
Some 2-(diethylamino)-7-hydroxy-4H-1-benzopyran-4-one derivatives, potentially useful as activators of the cystic fibrosis transmembrane conductance regulator (CFTR), were prepared. The synthesized compounds were tested, together with others 2-(dialkylami
MODIFICATION OF PHOTOCHEMICAL REACTIVITY BY CYCLODEXTRIN COMPLEXATION: SELECTIVITY IN PHOTO-CLAISEN REARRANGEMENT
Syamala, M, S.,Ramamurthy, V.
, p. 7223 - 7233 (2007/10/02)
Photorearrangements of meta-alkoxyphenylallyl ethers 1-5 in ethanol, in water and as complexes of α and β-cyclodextrins have been investigated.The ratio of the two ortho rearrangement products was dependent both on the lenght of the alkoxy substituent and on that of the host cavity suggesting that, subtle and rationale engineering manipulation is required to achieve exclusive obtention of only one ortho isomer.It is speculated that α-cyclodextrin provides a "tight fit" while β-cyclodextrin offers a "loose fit".This tightness of binding is suggested to be responsible for the selectivity among the ortho isomers with α-cyclodextrin as the host.Further, the results indicate that "loose cavity" can be tighttened by incorporating a "molecular spacer" such as a long hydrocarbon chain as an intramolecular appendix.
Process for the production of 2-aryl-2H-benzotriazoles
-
, (2008/06/13)
An improved process for the production of 2-aryl-2H-benzotriazoles by the reduction of o-nitroazobenzene intermediates with zinc in alkaline medium comprises employing a ratio of moles of alkali to moles of o-nitroazobenzene intermediate in the range of 0.2-1.7/1 in the presence of less than 150 ppm of iron based on zinc used. The improved process results in higher yields of high purity products with a concomitant reduction in the amount of undesired cleavage amine by-products and a reduction in effluent pollution problems. The process is carried out in a polar/non-polar solvent mixture.
