- From Monodisperse Thienyl- and Furylborane Oligomers to Polymers: Modulating the Optical Properties through the Hetarene Ratio
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The application of our newly developed B–C coupling method by catalytic Si/B exchange is demonstrated for the synthesis of a series of triarylboranes (1), monodisperse thienyl- and furylborane dimers (2) and trimers (9), extended oligomers (3) and polymers (3′), as well as mixed (oligo)thienyl-/furylboranes. The structures of 1 aaTip, 1 bbTip, and 2 bbbMes*, determined by X-ray crystallography, reveal largely coplanar hetarene rings and BR3 environments, which are most pronounced in the furylborane species. Photophysical investigations, supported by TD-DFT calculations, revealed pronounced π-electron delocalization over the hetarene backbones including the boron centers. With an extended series of derivatives of varying chain lengths available, we were able to determine the effective conjugation lengths (ECL) of poly(thienylborane)s and poly(furylborane)s, which have been reached with the highest-molecular-weight derivatives of our study. Through variation of the furan-to-thiophene ratio, the photophysical properties of these materials are effectively modulated. Significantly, higher furan contents lead to considerably increased fluorescence intensities. Compounds 1 aaTip, 1 bbTip, and 3 aTip showed the ability to bind fluoride anions. The binding process is signaled by a distinct change in their optical absorption characteristics, thus rendering these materials attractive targets for sensory applications.
- Lik, Artur,Jenthra, Sangeth,Fritze, Lars,Müller, Lars,Truong, Khai-Nghi,Helten, Holger
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Read Online
- Compound and organic luminescence display device
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The invention relates to the technical field of organic electroluminescent materials, in particular to a compound and an organic luminescence display device. The compound has a structure shown by formula (I) in the description, wherein D represents an electron donor unit; A represents an electron receiver unit; m and n are respectively and independently selected from 1, 2 or 3; in addition, the sum of the m and the n is smaller than or equal to 4. When the compound is used as a luminous material, an object material or a main body material of the organic luminescence display device, high luminescence efficiency can be realized.
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Paragraph 0187-0188
(2018/10/19)
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- Catalytic B-C Coupling by Si/B Exchange: A Versatile Route to π-Conjugated Organoborane Molecules, Oligomers, and Polymers
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Conjugated organoboranes have emerged as attractive hybrid materials for optoelectronic applications. Herein, a highly efficient, environmentally benign catalytic B-C bond formation method is presented that uses organosilicon compounds, dibromoboranes, and the metal-free organocatalyst Me3SiNTf2. This Si/B exchange approach has been successfully applied to the synthesis of arylborane molecules 4a-c, oligomers 8a,b, and polymers 8a′,b′. Photophysical investigations, supported by TD-DFT calculations, reveal highly effective π-conjugation in thienyl- and furylborane species; the latter are also highly emissive.
- Lik, Artur,Fritze, Lars,Müller, Lars,Helten, Holger
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p. 5692 - 5695
(2017/05/04)
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- The Daphniphyllum Alkaloids: Total Synthesis of (-)-Calyciphylline N
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Presented here is a full account on the development of a strategy culminating in the first total synthesis of the architecturally complex daphniphyllum alkaloid, (-)-calyciphylline N. Highlights of the approach include a highly diastereoselective, intramo
- Shvartsbart, Artem,Smith, Amos B.
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supporting information
p. 3510 - 3519
(2015/03/30)
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- Access to ultra-high-molecular weight poly(ethylene) and activity boost in the presence of cyclopentene with group 4 bis-amido complexes
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ZrIV complexes of the type [Me2Si{(NR)(6-{2-(diethylboryl) phenyl} pyridyl-2-yl-N)}ZrCl2 thf] (R=tBu (4), adamantyl (7a); thf= tetrahydrofuran), [Me2Si{(NAd)(6-{2-(diphenylboryl)phenyl}pyridyl- 2-yl-N)}ZrCl2] (Ad=adamantyl (7b)), the
- Narayana, Gurram Venkata,Xu, Guangjuan,Wang, Dongren,Frey, Wolfgang,Buchmeiser, Michael R.
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p. 151 - 162
(2014/03/21)
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- Total synthesis of (-)-calyciphylline N
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The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder re
- Shvartsbart, Artem,Smith, Amos B.
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supporting information
p. 870 - 873
(2014/02/14)
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- Steric control of geminal Lewis pair behavior: Frustration induced dyotropic rearrangement
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A series of methylene-linked boron/nitrogen geminal Lewis pairs were synthesized and the impacts of sterical effect on their chemical behavior were systematically investigated. Increasing the steric demand around the boron atom is manifested first by an incremental change in the structure of the resulting dative adducts. Accordingly, in the case of phenyl substituents (Alk 2NCH2BPh2), formation of head-to-tail dimers/oligomers was observed, while such an intermolecular association was avoided when o-tolyl moiety was introduced [Alk2NCH 2B(o-Tol)2], affording only an intramolecular dative complex. Further increase of sterical hindrance to a point (i.e. using mesityl substituents), however, caused a radical change in the structure; a dyotropic rearrangement occurred. Thus, steric interference induced a rearrangement in the geminal pair to relieve or minimize the frustration strain. Georg Thieme Verlag Stuttgart New York.
- Dorkó, éva,Varga, Eszter,Gáti, Tamás,Holczbauer, Tamás,Pápai, Imre,Mehdi, Hasan,Soós, Tibor
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supporting information
p. 1525 - 1528
(2014/07/08)
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- Bidirectional transfer of phenyl and methyl groups between PtIV and boron in platinum dipyridylborato complexes
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In the presence of weakly Lewis basic DMSO methyl group migration between B and PtIV in dipyridylborato trihydrocarbyl PtIV complexes is reversible; the preferred direction of Ph group migration in THF solution is from PtIV/sup
- Khaskin, Eugene,Zavalij, Peter Y.,Vedernikov, Andrei N.
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supporting information; experimental part
p. 10088 - 10089
(2009/02/04)
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- TRANSITION METAL COMPOUNDS WITH DONOR-ACCEPTOR INTERACTION AND A SPECIAL SUBSTITUTION PATTERN
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The invention relates to compounds, in which a transition metal comprising at least two ligand systems is complexed and at least two of said systems are reversibly linked to one another by at least one bridge consisting of a donor and an acceptor, whereby at least one fluorenyl ligand is included and at least one substituent of the acceptor group is an alkyl or aryl radical. The invention also relates to the use of said compounds with donor-acceptor interaction as polymerisation catalysts for producing high-molecular elastomers.
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Page/Page column 33-34
(2010/02/06)
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- Darstellung von Arylhalogenboranen
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In a ligand-exchange reaction between aryltrimethylsilanes, (ArSiMe3) and halogenboranes, (BX3 or ArBX2), arylhalogenboranes (ArBX2, ArAr'BX or Ar2BX) and halogentrimethylsilane are formed.This transfer of substituted aromatic groups from a silicon to a boron atom is an efficient synthetic pathway for the preparation of the corresponding arylhalogenboranes and diarylhalogenboranes with different aryl groups.Physical properties and spectroscopical data of the new arylhalogenboranes are given.
- Haubold, Wolfgang,Herdtle, Joerg,Gollinger, Walter,Einholz, Wolfgang
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