3598-30-9Relevant academic research and scientific papers
Butterfly Mesogens Based on Carbazole, Fluorene or Fluorenone: Mesomorphous, Gelling, Photophysical, and Photoconductive Properties
Hang, Jun-Fang,Lin, Hang,Zhao, Ke-Qing,Hu, Ping,Wang, Bi-Qin,Monobe, Hirosato,Zhu, Chenhui,Donnio, Bertrand
, p. 1989 - 2002 (2021)
We report a straightforward and generic synthesis of several new series of annulated π-extended poly-(hetero)aromatic hydrocarbons (PAH), with carbazole, fluorene and fluorenone central building blocks by the Suzuki-Miyaura/Scholl tandem reactions. The corresponding series of ditriphenylene discogens with a carbazole or a fluorenone central core, respectively, possess hexagonal columnar mesophases with broad mesophase ranges and high clearing points, as well as demonstrate a strong aggregation tendency in organic solvents as supergelators. The laterally-substituted ditriphenylene mesogens based on dimethyl-fluorene core exhibit a rich polymorphism with rectangular and hexagonal columnar mesophases from low temperatures onward, whereas their dioctyl-fluorene homologues melt directly into the isotropic liquid without showing mesophases. These latter family of compounds are luminescent with very high fluorescent quantum yields, of around 70 % in solution, and show outstanding photocurrent behavior with charge carrier mobility in the 10?2 cm2 V?1 s?1 range, as measured by photocurrent transient time-of-flight (TOF) technique. This straightforward molecular design and simple synthetic strategy proved to be both potent and resilient, and could be generally applied to the fabrication of a great variety of other heteroarene molecular systems as organic semiconductors and electroluminescent materials for potentially low-cost applications.
Board-like Fused-Thiophene Liquid Crystals and their Benzene Analogs: Facile Synthesis, Self-Assembly, p-Type Semiconductivity, and Photoluminescence
Zhao, Kai-Chun,Du, Jun-Qi,Wang, Hai-Feng,Zhao, Ke-Qing,Hu, Ping,Wang, Bi-Qin,Monobe, Hirosato,Heinrich, Beno?t,Donnio, Bertrand
, p. 462 - 470 (2019)
Fused-thiophene discotic liquid crystals were designed and easily synthesized by Suzuki coupling and FeCl3 oxidized tandem cyclodehydrogenation reactions, including homo- and cross-coupling reactions. The resulting hexagonal and rectangular columnar mesomorphic supramolecular structures formed were characterized by polarizing optical microscopy, differential scanning calorimetry, and small-angle X-ray scattering. The charge carrier transport properties in the mesophases of two of the synthesized fused-thiophene discogens were measured by transient photocurrent time-of-flight (TOF) technique, revealing fast hole transport values in the range of 10?3 to 10?2 cm2 V?1 s?1, thus demonstrating potential applications in electronic devices. The luminescent sanidic mesogens, with different extended π-conjugated systems, also emit blue, green, or red light, with absolute photoluminescent quantum yields as high as 18 %.
Electrochemical Control of Bridging Ligand Conformation in a Binuclear Complex-A Possible Basis for a Molecular Switch
Joulie, Laurent F.,Schatz, Erik,Ward, Michael D.,Weber, Frank,Yellowlees, Lesley J.
, p. 799 - 804 (1994)
Reaction of the binucleating bridging ligands 3,3',4,4'-tetrahydroxybiphenyl (H4L1) or 3,3",4,4"-tetrahydroxy-p-terphenyl (H4L2) with 2 equivalents of *2H2O (bipy = 2,2'-bipyridine) results in the formation of binuclear complexes (μ-L)>(2+) 1 (L = L1) and 2 (L = L2) in which the ligand L(4-) has been oxidized to the semiquinone (sq) form L(2-).In each complex the co-ordinated catecholate fragment (cat) may be oxidised reversibly to the semiquinone and quinone (q) redox states, giving the five-membered redox series cat-cat, cat-sq, sq-sq, sq-q and q-q for the bridging ligands.In the sq-sq state the bridging ligands are necessarily planar due to the presence of double bonds between the aromatic rings; in the cat-cat and q-q states there is formally no double-bond character between the aromatic rings and they are free to adopt a twisted conformation.Spectroelectrochemical measurements confirm that in the cat-cat and q-q states, 1 and 2 behave approximately like their mononuclear counterparts and (2+) ; for 1, the results also show that in the mixed-valence sq-q and sq-cat oxidation states the two halves of the ligand are electronically equivalent (i.e. valence delocalised), which is best explained by the bridging ligand retaining the planar confirmation of the sq-sq state.The change from planar to twisted therefore occurs at the extremes of the redox series, on formation of the cat-cat and q-q oxidation states.This control of bridging ligand conformation with oxidation state may form the basis for a molecular switch.
Synthesis of tetrahydroxybiphenyls and tetrahydroxyterphenyls and their evaluation as amyloid-β aggregation inhibitors
Stevens, Craig B.,Hanna Jr., James M.,Lammi, Robin K.
, p. 1703 - 1706 (2013)
3,3′,4,4′-Tetrahydroxybiphenyl and three isomeric 3,3″,4,4″-tetrahydroxyterphenyls with varying geometries around the central phenyl ring have been synthesized and evaluated for their in vitro activity against aggregation of Alzheimer's amyloid-β peptide (Aβ). Results from Congo red spectral-shift assays reveal that all four compounds successfully inhibit association of Aβ monomers. For the tetrahydroxyterphenyls, efficacy varies with linker geometry: the ortho-arrangement affords the most successful inhibition and the para-geometry the least, perhaps due to differing abilities of these compounds to bind Aβ. Of the four small molecules studied, 3,3′,4,4′- tetrahydroxybiphenyl is the most effective inhibitor, reducing Aβ aggregation by 50% when present in stoichiometric concentrations.
Hydroxylated biphenyls as tyrosinase inhibitor: A spectrophotometric and electrochemical study
Ruzza, Paolo,Serra, Pier Andrea,Fabbri, Davide,Dettori, Maria Antonietta,Rocchitta, Gaia,Delogu, Giovanna
, p. 1034 - 1038 (2016/12/26)
A small collection of C2-symmetry hydroxylated biphenyls was prepared by straightforward methods and the capability to act as inhibitors of tyrosinase has been evaluated by both spectrophotometric and electrochemical assays. Our attention was f
COMPOSITION
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, (2016/12/22)
Provided is a composition which comprises two immiscible compounds and a compatibiliser, which stabilises the interface between two or more immiscible compounds. The compatibiliser improves the morphology of blends comprising the first and second compounds. The composition may be useful in the context of functional blends for optoelectronic applications, such as solar cells, organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Also provided is a process for the preparation of the composition and compounds for use therein.
Conversion of Simple Cyclohexanones into Catechols
Liang, Yu-Feng,Li, Xinyao,Wang, Xiaoyang,Zou, Miancheng,Tang, Conghui,Liang, Yujie,Song, Song,Jiao, Ning
supporting information, p. 12271 - 12277 (2016/09/28)
A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.
Compound having four polymerizable groups, liquid crystal composition and liquid crystal display device
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, (2015/11/04)
A compound represented by formula (1), a liquid crystal composition, a liquid crystal display device are described. In formula (1), for example, the ring A1 and the ring A4 are phenylene or cyclohexylene; Z1, Z2
Novel features in the oxidation of dihydroxy benzenes by 2,6-dichloroquinone-4-chloro-imide in acetic acid and sodium acetate buffer medium
Madhavi,Syama Sundar,Radhakrishna Murti
, p. 242 - 245 (2007/10/03)
Kinetics of oxidation of quinol, catechol and resorcinol by 2,6-dichloroquinone-4-chloro-imide (DCQCI) in CH3COOH-NaOAc system is reported. The kinetic features of ortho dihydroxy and para dihydroxy benzenes are similar. The reactions are zero order in oxidant at lower concentrations of oxidant (below 0.0005 M) and fractional order in substrate. At higher concentrations of oxidant, these two compounds exhibit first order in oxidant and fractional order in substrate leading to independence. Resorcinol exhibits different kinetic features: first order in oxidant at all concentrations and fractional order in substrate. The major products are coupling products under these conditions. Reactivity order is resorcinol 〉 catechol 〉 quinol. This result is novel. A mechanism is postulated to explain the observed order and a suitable rate law has been derived.
Catalytic aerobic oxidative coupling of some simple phenols and natural phenanthrols with CuCl(OH).TMEDA
Majumder,Chakraborty,Roychowdhury
, p. 389 - 393 (2007/10/03)
Aerobic oxidative coupling of phenol, catechol, resorcinol and pyrogallol with CuCl(OH).TMEDA as catalyst affords 2',4-dihydroxybiphenyl (1a), 3,3',4,4'-tetrahydroxybiphenyl (2a), 2,2',4,4'-tetrahydroxybiphenyl (3a) and 2,2',4,6'-tetrahydroxybiphenyl (4a) and 2',3,3',4,4',5-hexahydroxybiphenyl (5a), respectively, in moderate yields. Similar catalytic aerobic oxidative coupling of the naturally occurring phenanthrols, nudol (6a) [2,7-dihydroxy-3,4-dimethoxyphenanthrene], 2,7-dihydroxy-3,4,6-trimethoxyphenanthrene (6b) and cirrhopetalin (7) [7-hydroxy-4-methoxy-2,3-methylenedioxyphenanthrene] with the same reagent gives the corresponding 1,1'-biphenanthryls 8a and 8c and the 8,8'-biphenanthryl 9a, respectively, in very good yields. All these reactions exhibit a high degree of regioselectivity.
