6630-80-4Relevant academic research and scientific papers
COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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Paragraph 0156-0159, (2021/11/02)
The compound is represented by chemical formula 1. 1 Is a cross-sectional view of an organic electronic device including an organic material layer between the first electrode, the first 2 electrode and the first 1 electrode, and 2. A compound represented
trans-N,N′-Bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine and its thioxanthenyl derivative as potential host compounds for the separation of anilines through host?guest chemistry principles
Barton, Benita,Hosten, Eric C.,Jooste, Daniel V.
, (2020/06/09)
In this work, we investigate the potential of separating mixtures of the guest solvents aniline (ANI), N-methylaniline (NMA) and N,N-dimethylaniline (DMA) by means of host?guest chemistry principles employing two novel host compounds, namely trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,2-diamine (1,2-DAX) and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,2-diamine (1,2-DAT). These aniline solvents may exist in such mixtures since NMA and DMA are often prepared from ANI by alkylation methods, and reaction yields are seldom quantitative. Owing to their similar boiling points, ranging from 184 to 196 oC, the more usual distillation techniques for their separation are challenging. After recrystallization experiments of the two host compounds from various combinations of these anilines, it was revealed that host?guest chemistry certainly has the potential to serve as an alternative separation strategy for such mixtures. Equimolar ANI/DMA solutions proved most successful, where both 1,2-DAX and 1,2-DAT showed near-quantitative selectivity for DMA (90%). Both single crystal diffraction and thermal analyses were employed in order to understand the preferential behaviour displayed by each host compound.
Synthesis and assessment of compounds trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,4-diamine and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,4-diamine as hosts for potential xylene and ethylbenzene guests
Barton, Benita,Jooste, Daniel V.,Hosten, Eric C.
, p. 333 - 346 (2019/03/23)
In this work, two novel compounds, trans-N,N′-bis(9-phenyl-9-xanthenyl)cyclohexane-1,4-diamine 1 and trans-N,N′-bis(9-phenyl-9-thioxanthenyl)cyclohexane-1,4-diamine 2, were designed and successfully synthesized in our laboratories, and assessed for their host potential in the presence of potential xylene (Xy) isomer and ethylbenzene (EB) guests. Host 1 successfully formed complexes with all four of o-Xy, m-Xy, p-Xy and EB, while 2 only clathrated p-Xy and EB. Equimolar guest/guest competition experiments showed that hosts 1 and 2 possess very similar selectivities for these guests [p-Xy (73.9%) > EB (13.0%) > m-Xy (8.1%) > o-Xy (5.0%) and p-Xy (71.3%) > EB (20.2%) > m-Xy (6.0%) > o-Xy (2.5%) for 1 and 2, respectively]. Single crystal diffraction analyses revealed striking geometry changes for the sulfur host analogue: while the tricyclic fused ring system of the oxygen host remained planar when guest was absent or present, this fused system of the sulfur analogue experienced a dramatic geometry change from buckled (in the absence of guest) to planar (in guest presence). This observation explained the selectivity similarities of both hosts in the presence of these guests. Additionally, the relative thermal stabilities of the four complexes with host 1 were assessed by employing thermal analyses, and the results of these correlated exactly with the selectivity order, since the onset temperature of the guest release processes (Ton) was in the order p-Xy (88.0?°C) > EB (70.9?°C) > m-Xy (59.7?°C) > o-Xy (46.2?°C). Ton values also explained the significant preference of host 2 for p-Xy (115.5?°C) relative to EB (76.6?°C), respectively.
A Sc(OTf)3 catalyzed dehydrogenative reaction of electron-rich (hetero)aryl nucleophiles with 9-aryl-fluoren-9-ols
Zhou, Chen,Hu, Chen,Hong, Gang,He, Yuchen,Tang, Zhicong,Wang, Limin
supporting information, p. 9615 - 9619 (2019/11/20)
A highly efficient dehydrogenative reaction of a series of nucleophiles with 9-aryl-fluoren-9-ols has been realized by using only 2 mol% of Sc(OTf)3 as a catalyst. The corresponding indole-containing 9,9-diarylfluorenes were obtained in up to 99% yield as well as other electron-rich (hetero)arene adducts. The protocol exhibits high selectivity, mild reaction conditions and good substrate compatibility (32 examples). This protocol is further highlighted by its applications in the construction of potential electroluminescent materials.
A comparison of the behaviour of two closely related xanthenyl-derived host compounds in the presence of vaporous dihaloalkanes
de Jager, Lize,Barton, Benita,Hosten, Eric C.
, p. 181 - 194 (2018/09/11)
The behaviour of two closely related xanthone-derived host compounds, N,N’-bis(9-phenyl-9-xanthenyl)ethylenediamine and N,N′-bis(9-phenyl-9-thioxanthenyl)ethylenediamine, which formed complexes with CH2Cl2, CH2Br2 and CH2I2 after recrystallization from each of these solvents, was compared when subjected to these guest and guest mixtures in the vapour phase. Surprisingly, these hosts displayed entirely different behaviours under these conditions, with only the thioxanthenyl derivative possessing the ability to clathrate these guests (or guest mixtures) from the gas phase; this ability was entirely absent in the xanthenyl host. All novel complexes were subjected to single crystal diffraction analyses in order to investigate the interactions present, as well as thermal and Hirshfeld surface experiments. The host selectivity and host–guest interactions were correlated with the differences observed in the recrystallization and vapour experiments. Furthermore, data obtained for the novel complexes by employing various analytical techniques were related back to the observed selectivity order.
Steric Effects on the Primary Isotope Dependence of Secondary Kinetic Isotope Effects in Hydride Transfer Reactions in Solution: Caused by the Isotopically Different Tunneling Ready State Conformations?
Maharjan, Binita,Raghibi Boroujeni, Mahdi,Lefton, Jonathan,White, Ormacinda R.,Razzaghi, Mortezaali,Hammann, Blake A.,Derakhshani-Molayousefi, Mortaza,Eilers, James E.,Lu, Yun
, p. 6653 - 6661 (2015/06/08)
The observed 1° isotope effect on 2° KIEs in H-transfer reactions has recently been explained on the basis of a H-tunneling mechanism that uses the concept that the tunneling of a heavier isotope requires a shorter donor-acceptor distance (DAD) than that of a lighter isotope. The shorter DAD in D-tunneling, as compared to H-tunneling, could bring about significant spatial crowding effect that stiffens the 2° H/D vibrations, thus decreasing the 2° KIE. This leads to a new physical organic research direction that examines how structure affects the 1° isotope dependence of 2° KIEs and how this dependence provides information about the structure of the tunneling ready states (TRSs). The hypothesis is that H- and D-tunneling have TRS structures which have different DADs, and pronounced 1° isotope effect on 2° KIEs should be observed in tunneling systems that are sterically hindered. This paper investigates the hypothesis by determining the 1° isotope effect on α- and β-2° KIEs for hydride transfer reactions from various hydride donors to different carbocationic hydride acceptors in solution. The systems were designed to include the interactions of the steric groups and the targeted 2° H/D's in the TRSs. The results substantiate our hypothesis, and they are not consistent with the traditional model of H-tunneling and 1° /2° H coupled motions that has been widely used to explain the 1° isotope dependence of 2° KIEs in the enzyme-catalyzed H-transfer reactions. The behaviors of the 1° isotope dependence of 2° KIEs in solution are compared to those with alcohol dehydrogenases, and sources of the observed "puzzling" 2° KIE behaviors in these enzymes are discussed using the concept of the isotopically different TRS conformations. (Figure Presented).
New method for the preparation of dibenzo[b,f][1,4]thiazepines
Fujii, Takayoshi,Hao, Wei,Yoshimura, Toshiaki
, p. 246 - 250 (2007/10/03)
The S-amination of 9H-thioxanthen-9-ol (2a) and 9-substituted derivatives 2b-e (Me (b), Et (c), iPr (d), Ph (e)) with O- mesitylenesulfonylhydroxylamine (MSH) was carried out. The expected product, 10-amino-9-hydroxy-9-isopropyl-9H-thioxanthenium mesitylenesulfonate (3d), was obtained in 78% yield from the corresponding thioxanthen-9-ol 2d. However, in the case of 2a-c and 2e the reaction led instead to dibenzo[b, f][1,4]thiazepines 6a-c and 6e in moderate yields.
Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes
Kinoshita, Sayaka,Kinoshita, Hironori,Iwamura, Tatsunori,Watanabe, Shin-ichi,Kataoka, Tadashi
, p. 1496 - 1502 (2007/10/03)
Reactions of but-3-yn-2-one (2) with aldehydes 1 in the presence of a Lewis acid and dimethyl sulfide (3a) predominantly gave (E)-α-(halomethylene)aldols 4-5 in high yields, while reactions of methyl propiolate (6a) mainly afforded (Z)-3-halogeno-2-(hydro
S-pixyl analogues as photocleavable protecting groups for nucleosides
Coleman, Michael P.,Boyd, Mary K.
, p. 7641 - 7648 (2007/10/03)
Several analogues of the 9-phenylthioxanthyl (S-pixyl) photocleavable protecting group have been synthesized, containing substituents on the 9-aryl ring and on the thioxanthyl backbone. Each analogue protected the 5′-hydroxy moiety of thymidine in good to excellent yield. The protected substrates were deprotected in 1:1 water: acetonitrile with irradiation at 300 nm, resulting in recovered thymidine in excellent yield, except for the nitro-substituted analogues which gave substantially lower yields. Substrates with 2,7-dibromo or 3-methoxy substitution on the thioxanthyl backbone were also deprotected efficiently with irradiation at 350 nm. Shorter irradiation times were observed in the less nucleophilic solvent mixture of 1:9 trifluoroethanol: acetonitrile, with no formation of secondary photooxidation products. Photodeprotection with high yields was also achieved in the absence of solvent, with no secondary photoproducts.
9-Phenylxanthen-9-ylium and 9-phenylthioxanthen-9-ylium ions: Comparison of o- and p-substitutions in the 9-phenyl group by cyclic voltammetry and visible spectra
Erabi, Tatsuo,Asahara, Masahiro,Miyamoto, Masahumi,Goto, Keisuke,Wada, Masanori
, p. 1325 - 1332 (2007/10/03)
9-Arylxanthen-9-ylium (3a-i) and 9-arylthioxanthen-9-ylium (4a,b,e-i) perchlorates [aryl = 2,4,6-(MeO)3C6H2 (a), 2,6-(MeO)2C6H3 (b), 2-MeOC6H4 (c), 4-MeOC6H4 (d), 3-Br-2,6-(MeO)2C6H2 (e), 2,4,6-Me3C6H2 (f), 2-MeC6H4 (g), 4-MeC6H4 (h), C6H5 (i)] were prepared by the reactions of 9-arylxanthen-9-ols or 9-arylthioxanthen-9-ols with perchloric acid. Their LUMO and HOMO levels were estimated from the redox potential (E0) in cyclic voltammetry and λmax in the UV-visible spectra measured for a 1,2-dichloroethane solution, and were compared with those of 9-aryl-1,8-dimethoxyxanthen-9-ylium ions (8b,i). We found that 1) both the LUMO and HOMO levels varied almost in the same order of substituent on the 9-phenyl group; 2) the MeO-group on the 9-phenyl group was more effective to raise both the HOMO and LUMO levels than the Me-group; 3) the HOMO levels of 3 and 4 were more sensitive than the LUMO levels to the change in the 9-aryl group; 4) p-substitution by MeO- or Me-groups was more effective to raise the HOMO and LUMO levels than o-substitution; 5) the presence of two o-MeO groups was more effective to raise the HOMO and LUMO levels than one o-MeO group; 6) a m-bromination of 9-aryl group in 3b or 4b greatly lowered both LUMO and HOMO levels, as observed for 3e or 4e; 7) both the HOMO and LUMO levels of 8b and 8i were higher than those of 3b and 3i, respectively; 8) the LUMO level of 3b was higher than that of 8i, the isomer.
