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1.
Synthesis of Functionalized Mono‐, Bis‐, and Trisethynyltriptycenes for One‐Dimensional Self‐Assembly on Surfaces
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Agnès M. Sirven Romain Garbage Yun Qiao Dr. Claire Kammerer Prof. Dr. Gwénaël Rapenne 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(42):15013-15019
This paper describes the synthesis of triptycene‐based building blocks that are able to interact through hydrogen bonds to form one‐dimensional self‐assembled motifs on surfaces. We designed 9,10‐diethynyltriptycene derivatives functionalized at the ethynyl end groups by a variety of hydrogen‐bonding groups for homomolecular recognition and complementary building blocks for heteromolecular recognition. We also present the synthesis of bis‐ and trisethynyltriptycenes with terminal alkyne functional groups available for on‐surface azide–alkyne cycloaddition reaction to expand the potential of the triptycene building block. 相似文献
2.
Triptycene‐Based Chiral Macrocyclic Hosts for Highly Enantioselective Recognition of Chiral Guests Containing a Trimethylamino Group
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Geng‐Wu Zhang Peng‐Fei Li Zheng Meng Han‐Xiao Wang Ying Han Prof. Chuan‐Feng Chen 《Angewandte Chemie (International ed. in English)》2016,55(17):5304-5308
A new class of chiral macrocyclic arene composed of three chiral 2,6‐dihydroxyltriptycene subunits bridged by methylene groups was designed and synthesized. Structural studies showed that the macrocyclic molecule adopts a hex‐nut‐like structure with a helical chiral cavity and highly fixed conformation. Efficient resolution was achieved through the introduction of chiral auxiliaries to give a couple of enantiopure macrocycles, which exhibited high enantioselectivity towards three pairs of chiral compounds containing a trimethylamino group. 相似文献
3.
Blurring the Lines between Host and Guest: A Chimeric Receptor Derived from Cucurbituril and Triptycene
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Dr. Xiaoyong Lu Dr. Soumen K. Samanta Dr. Peter Y. Zavalij Prof. Dr. Lyle Isaacs 《Angewandte Chemie (International ed. in English)》2018,57(27):8073-8078
We report the synthesis and X‐ray crystal structure of a cucurbituril–triptycene chimeric receptor ( 1 ). Host 1 binds to guests typical of CB[6]–CB[8], but also binds to larger guests such as blue box ( 20 ) and the Fujita square ( 22 ). Intriguingly, the geometries of the 1 ? 20 and 1 ? 22 complexes blur the lines between host and guest in that both components fulfill both roles within each complex. The fluorescence output of 1 is fully quenched by the formation of complexes with pyridinium‐derived guests. 相似文献
4.
New iodotriptycenes, including some chiral derivatives, have been synthesised, and their catalytic potential towards oxidative transformations has been investigated. The enantioselectivities observed in the products using chiral iodotriptycene catalysts are low, probably owing to the large distances between the coordinating groups and the iodine moieties in these compounds. 相似文献
5.
Yukimasa Aida Dr. Yu Shibata Prof. Dr. Ken Tanaka 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(14):3004-3009
The enantioselective synthesis of distorted π-extended chiral triptycenes, consisting of three distinct aromatic rings, has been achieved with high ee value of 87 % by the cationic rhodium(I)/segphos complex-catalyzed enantioselective [2+2+2] cycloaddition of 2,2′-di(prop-1-yn-1-yl)-5,5′-bis(trifluoromethyl)-1,1′-biphenyl with 6-methoxy-1,2-dihydronaphthalene followed by the diastereoselective Diels–Alder reaction and aromatization. Demethoxy derivatives were also synthesized by the C−O bond cleavage. In this synthesis, the use of the electron-deficient diyne and the electron-rich alkene is crucial to suppress the undesired strain-relieving carbocation rearrangement and stabilize the distorted triptycene structure. 相似文献
6.
Attractive Dispersion Interactions Versus Steric Repulsion of tert‐Butyl groups in the Crystal Packing of a D3h‐Symmetric Tris(quinoxalinophenanthrophenazine)
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Bernd Kohl Mercedes V. Bohnwagner Dr. Frank Rominger Prof. Dr. Hubert Wadepohl Prof. Dr. Andreas Dreuw Prof. Dr. Michael Mastalerz 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(2):646-655
The crystalline packing of a π‐extended D3h‐symmetric triptycene reveals a particular π stacking motif with an almost‐eclipsed arrangement of adjacent π planes despite the steric repulsion of tert‐butyl substituents. Four model compounds were analyzed by using single‐crystal X‐ray diffraction and theoretical calculations to study the influence of dispersion interactions of molecular parts and understand the relationship between the molecular structure and this unique packing motif. 相似文献
7.
Min Xue Yong‐Sheng Su Chuan‐Feng Chen Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(28):8537-8544
On the basis of formation of [2]pseudorotaxane complexes between triptycene‐derived tetralactam macrocycles 1 a and 1 b and squaraine dyes, construction of squaraine‐based [2]rotaxanes through clipping reactions were studied in detail. As a result, when two symmetrical squaraines 2 d and 2 e were utilized as templates, two pairs of isomeric [2]rotaxanes 3 a – b and 4 a – b as diastereomers were obtained, owing to the two possible linking modes of triptycene derivatives. It was also found, interestingly, that when a nonsymmetrical dye 2 g was involved, there existed simultaneously three isomers of [2]rotaxanes in one reaction due to the different directions of the guest threading. The 1H NMR and 2D NOESY NMR spectra were used to distinguish the isomers, and the yield of [2]rotaxane 5 a with the benzyl group in the wider rim of the host 1 a was found to be higher than that of another isomer 5 b with an opposite direction of the guest, which indicated the partial selection of the threading direction. The X‐ray structures of 3 b and 4 a showed that, except for the standard hydrogen bonds between the amide protons of the hosts and the carbonyl oxygen atoms of the guests, multiple π???π stacking and C? H???π interactions between triptycene subunits and aromatic rings of the guests also participated in the complexation. Crystallographic studies also revealed that the [2]rotaxane molecules 3 b and 4 a further self‐assembled into tubular structures in the solid state with the squaraine dyes inside the channels. In the case of 4 a , all the nonsymmetrical macrocyclic molecules pointed in one direction, which suggests the formation of oriented tubular structures. Moreover, it was also found that the squaraines encapsulated in the triptycene‐derived macrocycles were protected from chemical attack, and subsequently have potential applications in imaging probes and other biomedical areas. 相似文献
8.
9.
Triptycenes are an intriguing class of organic molecules with several unusual characteristics, such as a propeller-like shape, saddle-like cavities around a symmetrical scaffold, a rigid π-framework. They have been extensively studied and proposed as key synthons for a variety of applications in supramolecular chemistry and materials science. When decorated with an appropriate substitution pattern, triptycenes can be chiral, and, similarly to other popular chiral π-extended synthons, can express chirality robustly, efficiently, and with relevance to chiroptical spectroscopies. This minireview highlights and encompasses recent advances in the synthesis of chiral triptycenes and in their introduction as molecular scaffolds for the assembly of functional supramolecular materials. 相似文献
10.
N A A Al-Jabar J Bowen Jones D S Brown A H Colligan A G Massey J M Miller J W Nye 《应用有机金属化学》1989,3(6):459-468
Mass and NMR spectral data are presented for a number of dodecafluoro-1,6-disubstituted triptycenes. The epoxide OAs2(C6F4)2 can be made by heating together arsenic (As), arsenic(III) oxide (As2O3) and 1,2-di-iodotetrafluorobenzene (1,2-I2C6F4) in a sealed tube. The molecular structure of As2(C6F4)3 has been confirmed by X-ray crystallography. 相似文献