134080-67-4Relevant academic research and scientific papers
Copper-Free Sonogashira Coupling for High-Surface-Area Conjugated Microporous Poly(aryleneethynylene) Networks
Trunk, Matthias,Herrmann, Anna,Bildirir, Hakan,Yassin, Ali,Schmidt, Johannes,Thomas, Arne
, p. 7179 - 7183 (2016)
A modified one-pot Sonogashira cross-coupling reaction based on a copper-free methodology has been applied for the synthesis of conjugated microporous poly(aryleneethynylene) networks (CMPs) from readily available iodoarylenes and 1,3,5-triethynylbenzene. The polymerization reactions were carried out by using equimolar amounts of halogen and terminal alkyne moieties with extremely small loadings of palladium catalyst as low as 0.65 mol %. For the first time, CMPs with rigorously controlled structures were obtained without any indications of side reactions, as proven by FTIR and solid-state NMR spectroscopy, while showing Brunauer-Emmett-Teller (BET) surface areas higher than any poly(aryleneethynylene) network reported before, reaching up to 2552 m2 g-1. A modified one-pot Sonogashira cross-coupling reaction based on a copper-free methodology has been applied for the synthesis of conjugated microporous polymers (CMPs). Not only are the resulting structures much more defined than previously published materials, but they also show far superior Brunauer-Emmett-Teller (BET) surface areas of up to 2552 m2 g-1, setting a new record for this type of materials (see scheme).
Tetrastyrylmethane
Su, Dan,Menger
, p. 1485 - 1488 (1997)
The first synthesis of tetrastyrylmethane is reported.
Synthesis of Highly Fluoroalkyl-Functionalized Oligoporphyrin Systems
Felix, Lukas,Sezer, Ugur,Arndt, Markus,Mayor, Marcel
, p. 6884 - 6895 (2014)
Four different multiporphyrin systems have been synthesized and characterized. Highly fluoroalkyl-functionalized porphyrins are the most complex objects so far to have exhibited quantum wave nature. We have functionalized larger oligoporphyrin systems with fluoroalkyl chains to increase their mass and minimize their intermolecular interactions. The to-some-extent random substitution of fluorine atoms at the periphery of the oligoporphyrins results in libraries consisting of molecules varying in both the number and spatial distribution of substituents. The mass-selected individual members of these libraries were designed for quantum interference experiments. To investigate the volatilization nature of the molecules within the library, laser desorption and post-ionization studies were performed. These studies demonstrated that molecular beams of suitable velocity and ionization cross-section can be obtained from these libraries. In particular, we present these features for two libraries, based on either a tetrahedrally arranged central porphyrin tetramer or a more planar porphyrin pentamer.
Supramolecular Nanopatterns of Molecular Spoked Wheels with Orthogonal Pillars: The Observation of a Fullerene Haze
Grimme, Stefan,H?ger, Sigurd,Jester, Stefan-S.,Jochemich, Anna,Keller, Tristan J.,Kr?nert, Anna,Müller, Ute,Poluektov, Georgiy,Spicher, Sebastian
supporting information, p. 27264 - 27270 (2021/11/30)
Molecular spoked wheels with intraannular functionalizable pillars are synthesized in a modular approach. The functionalities at their ends are variable, and a propargyl alcohol, a [6,6]-phenyl-C61-butyrate, and a perylene monoimide are investigated. All compounds form two-dimensional crystals on highly oriented pyrolytic graphite at the solid–liquid interface. As determined by submolecularly resolved scanning tunneling microscopy, the pillars adopt equilibrium distances of 6.0 nm. The fullerene has a residual mobility, limited by the length of the flexible connector unit. The experimental results are supported and rationalized by molecular dynamics simulations. These also show that, in contrast, the more rigidly attached perylene monoimide units remain oriented along the surface normal and maintain a smallest distance of 2 nm above the graphite substrate. The robust packing concept also holds for cocrystals with molecular hexagons that expand the pillar–pillar distances by 15 % and block unspecific intercalation.
Synthesis of Rigid Rod, Trigonal, and Tetrahedral Nucleobase-Terminated Molecules
Cheng, Liang,Jin, Xiao-Yang,Liu, An-Di,Liu, Li,Wu, Chuan-Shuo
, (2022/01/12)
An efficient fragment splicing method for the construction of multiple nucleobase-terminated monomers has been developed. Conformationally fixed rod, trigonal planar and tetrahedral thymine and adenine structures were generated in moderate to good yields,
Divergent Synthesis of Porous Tetraphenylmethane Dendrimers
Urzúa, Julio I.,Torneiro, Mercedes
, p. 13231 - 13238 (2017/12/26)
Tetraphenylmethane-ethynylene-based shape-persistent dendrimers are a new class of nanoobjects with an intriguing 3D architecture. We report an efficient divergent strategy for their synthesis based on the Sonogashira Pd-catalyzed coupling of terminal alkynes with aryl iodides. As repeat unit, we prepared a tetraphenylmethane derivative bearing a terminal alkyne and three triazene moieties. Coupling of this building block to tetrakis(p-iodophenyl)methane afforded, after triazene activation, a dodecaiodo-terminated first generation dendrimer, which was transformed by another Sonogashira coupling into a methoxy-terminated second generation dendrimer with persistent globular shape and well-defined cavities. This work also unveils new aspects of triazene chemistry, i.e., the unprecedented efficient generation of an azo compound by mixing of a triazene with phenol.
Preparation of functionalised tetraphenylmethane derivatives via the Suzuki-Miyaura cross-coupling reaction
Kotha, Sambasivarao,Behera, Manoranjan
, p. 2684 - 2689 (2007/10/03)
A general methodology for the synthesis of various symmetrical and unsymmetrical tetraphenylmethane (TPM) derivatives is reported using the Suzuki-Miyaura (SM) cross-coupling reaction as a key step. The formation of an interesting self-coupling product 14 during the SM cross-coupling reaction of mono-iodo tetraphenylmethane derivative 5 is also observed.
Nanoscale 1,3,5,7-tetrasubstituted adamantanes and p-substituted tetraphenyl-methanes for AFM applications.
Li, Quan,Rukavishnikov, Aleksey V,Petukhov, Pavel A,Zaikova, Tatiana O,Keana, John F W
, p. 3631 - 3634 (2007/10/03)
[structure: see text] Tetrahedrally shaped nanoscale molecules 18-20 were synthesized from the corresponding tetraiodide by a series of Sonogashira coupling reactions. Three of the sulfur-containing termini are intended for eventual binding to a gold-coat
Tetrahedral onsager crosses for solubility improvement and crystallization bypass
Aujard,Baltaze,Baudin,Cogne,Ferrage,Jullien,Perez,Prevost,Lin Mao Qian,Ruel
, p. 8177 - 8188 (2007/10/03)
Pure organic molecules exhibiting a suitable concave rigid shape are expected to give porous glasses in the solid state. Such a feature opens new opportunities to avoid crystallization and to improve molecular solubility in relation to the high internal energy of these solid phases. To quantitatively explore the latter strategy, a series of rigid tetrahedral conjugated molecules nC and the corresponding models nR have been synthesized. Related to the present purpose, several properties have been investigated using UV absorption, steady-state fluorescence emission, differential scanning calorimetry, 1H NMR translational self-diffusion, magic angle spinning 13C NMR, and multiple-beam interferometry experiments. The present tetrahedral crosses are up to 8 orders of magnitude more soluble than the corresponding model compounds after normalization to the same molecular length. In addition, they give concentrated monomeric solutions that can be used to cover surfaces with homogeneous films whose thickness goes down to the nanometer range. Such attractive features make cross-like molecular architectures promising for many applications.
