435-08-5Relevant academic research and scientific papers
Preparation of Recyclable and Versatile Porous Poly(aryl thioether)s by Reversible Pd-Catalyzed C–S/C–S Metathesis
Morandi, Bill,Rivero-Crespo, Miguel A.,Toupalas, Georgios
supporting information, p. 21331 - 21339 (2021/12/17)
Porous organic materials (polymers and COFs) have shown a number of promising properties; however, the lability of their linkages often limits their robustness and can hamper downstream industrial application. Inspired by the outstanding chemical, mechanical, and thermal resistance of the 1D polymer poly(phenylene sulfide) (PPS), we have designed a new family of porous poly(aryl thioether)s, synthesized via a mild Pd-catalyzed C–S/C–S metathesis-based method, that merges the attractive features common to porous polymers and PPS in a single material. In addition, the method is highly modular, allowing to easily introduce application-oriented functionalities in the materials for a series of environmentally relevant applications including metal capture, metal sensing, and heterogeneous catalysis. Moreover, despite their extreme chemical resistance, the polymers can be easily recycled to recover the original monomers, offering an attractive perspective for their sustainable use. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new, recyclable materials.
Fluorination of the tetraphenylethene core: Synthesis, aggregation-induced emission, reversible mechanofluorochromism and thermofluorochromism of fluorinated tetraphenylethene derivatives
Zhang, Hao,Nie, Yong,Miao, Jinling,Zhang, Dengqing,Li, Yexin,Liu, Guangning,Sun, Guoxin,Jiang, Xuchuan
supporting information, p. 3306 - 3314 (2019/03/19)
The Suzuki-Miyaura cross-coupling reactions of bromoalkenes with fluorophenylboronic acids afforded 17 fluorinated tetraphenylethene (FTPE) compounds that have only fluorine substituent(s) directly on the tetraphenylethene (TPE) core with different number
Halogenated tetraphenylethene with enhanced aggregation-induced emission: An anomalous anti-heavy-atom effect and self-reversible mechanochromism
Xu, Pengfei,Qiu, Qianqian,Ye, Xinru,Wei, Mengru,Xi, Wenbin,Feng, Hui,Qian, Zhaosheng
supporting information, p. 14938 - 14941 (2019/12/24)
Halogenated tetraphenylethene derivatives show a unique anti-heavy-atom effect where introducing heavy halogens like bromine greatly improves the fluorescence quantum yield upon aggregation, contrary to the classic heavy-atom effect. The unique self-reversible mechanochromism of brominated TPE is attributed to re-generation of halogen-halogen bonding after its breakage.
Fluorotetraphenyl ethylene derivative as well as preparation method and use thereof
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Paragraph 0218; 0219; 0220, (2018/11/22)
The invention discloses a fluorotetraphenyl ethylene derivative as well as a preparation method and use thereof, and belongs to the field of organic synthesis and luminescent materials. The derivativecomprises the following structure: shown in the description, wherein, when R1-R2 are H, at least one of the substituents R3-R7 is F, and at least one of the substituents R8-R12 is F; when R1 to R7 are both H, at least 1 and at most 3 of the substituents of R8-R12 are F; when R2 is F and R1 is H, at least one of the substituents R3-R7 is F, and at least one of the substituents R8-R12 is F; when R1and R2 are both F, at least one of the substituents R3-R7 is F, and at least one of the substituents R8-R12 is F. The fluorinetetraphenyl ethylene-containing derivative provided by the invention hasthe characteristics of aggregation-induced emission and force-induced fluorescence discoloration, can be used in the fields of luminescent materials, biological probes and chemical sensing, and has extensive application prospects.
Stereoselective synthesis of olefins by a reductive coupling reaction
Hua, Guoxiong,Li, Yang,Slawin, Alexandra M. Z.,Woollins, J. Derek
, p. 1477 - 1480 (2007/10/03)
Ketones and aldehydes are converted to symmetrical and (E)-olefins (1-15) by reaction with 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (PhPSe2)2, Woollins' reagent, in refluxing toluene; use of diketones was demonstrated by the reaction of PhC(O)CH2C(O)Ph which gives 1,2,4,5-tetraphenylbenzene (16) in 83% yield. The Royal Society of Chemistry 2007.
Dications of fluorenylidenes. Relationship between electrochemical oxidation potentials and antiaromaticity in diphenyl-substituted fluorenyl cations
Mills, Nancy S.,Benish, Michele A.,Ybarra, Christie
, p. 2003 - 2012 (2007/10/03)
The antiaromaticity of a series of dications of p-substituted diphenylmethylidene fluorenes was explored using three criteria attributed to aromaticity/antiaromaticity. The relative stability of the dications (energetic criterion) was measured via the red
Stereochemistry of the [4 + 2] cycloaddition of diarylselenoketones with conjugated dienes
Wilker, Stefanie,Erker, Gerhard
, p. 10922 - 10930 (2007/10/03)
The ylides Ph3P=CAr1Ar2 1a-g (Ar = C6H5, p-C6H4Cl, p-C6H4F, m-C6H4CF3, p-C6H4OCH3, p-C6H4-CH3) were treated with elemental selenium (～80°C) to give the corresponding selenoketones Se=CAr1Ar2 2 by Staudinger-chalcogenation. Their reaction with trans,trans-2,4-hexadiene proceeds completely stereospecifically to yield the 2,2-diaryl-3,6-dihydro-cis-3,6-dimethyl-2H-selenapyrans 3. In contrast, the reactions of the selenoketones 2 with cis,trans-2,4-hexadiene proceeds stereoselectively, also giving the dihydro-cis-dimethyl-2H-selenapyrans 3 as the major products, now admixed with small amounts of the dihydro-trans-dimethyl-2H-selenapyran isomers 4. The [4 + 2] cycloaddition of 2 with cis,trans-2,4-hexadiene proceeds stereospecifically, however, when carried out at a pressure of 12 kbar, now yielding 4 as the major products along with the corresponding tetraarylethenes 8. Along with the results of additional mechanistic studies (determination of solvent and substituent effects) it can be concluded that diarylselenoketones are likely to react by means of a concerted [4 + 2] cycloaddition with very reactive conjugated dienes (such as trans,trans-2,4-hexadiene), whereas a stepwise mechanism, resulting in diene cis/trans-isomerization with subsequent mechanistic "leakage" to the concerted pathway, appears to be preferred when a much less reactive conjugated diene such as cis,trans-2,4-hexadiene is employed. The reaction of the corresponding diarylthioketones 5a-g with trans,trans- and cis,trans-2,4-hexadiene, respectively, shows an analogous behavior.
FACILE CONVERSION, USING A VASTLY IMPROVED GATTERMAN PROCEDURE, OF ACTIVATED THIOBENZOPHENONES INTO TETRAARYLETHYLENES.
Baran, Janusz,Laszlo, Pierre
, p. 5135 - 5136 (2007/10/02)
A simple and inexpensive procedure is proposed for the title couplig, performed at room temperature in DMSO.
