918826-08-1Relevant articles and documents
2-Azidoethane-1-sulfonylfluoride (ASF): A Versatile Bis-clickable Reagent for SuFEx and CuAAC Click Reactions
Zhang, Xu,Moku, Balakrishna,Leng, Jing,Rakesh,Qin, Hua-Li
supporting information, p. 1763 - 1769 (2019/02/24)
A new reagent, 2-azidoethane-1-sulfonylfluoride (ASF), was synthesized from 2-chloroethane-1-sulfonyl fluoride in 50g-scale with 87 % yield. This novel reagent possesses two selectively clickable functionalities to be used for both CuAAC and SuFEx click reactions. The application of this reagent ASF to the construction of a class of novel 1,2,3-triazole derived S(VI)-F analogs was achieved in a quick, efficient and atom-economical manner. Orthogonally clickable construction of a new class of dendrimers was also accomplished.
Naphthalimide-containing conjugated polyelectrolytes with different chain configurations
Chen, Yu,Tan, Ying,Tan, Chunyan,Lu, Yunpeng,Chen, Yuzong,Jiang, Yuyang
supporting information, p. 2635 - 2639 (2019/03/13)
Several donor-acceptor type conjugated polyelectrolytes containing naphthalimide are developed. Different polymer chain configurations of the backbones of polymers lead to different photophysical properties. The para-substituted polymers show extended conformations with quite low quantum yields in high polarity solvents because of twisted intramolecular charge transfer features, while the meta-substituted polymers can form helices and demonstrated significantly improved quantum yields in water and methanol, as well as achieving sensitive, ultrafast and ratiometric detection of trace methylene blue in water.
H-Bonded Duplexes based on a Phenylacetylene Backbone
Swain, Jonathan A.,Iadevaia, Giulia,Hunter, Christopher A.
supporting information, p. 11526 - 11536 (2018/09/18)
Complementary phenylacetylene oligomers equipped with phenol and phosphine oxide recognition sites form stable multiply H-bonded duplexes in toluene solution. Oligomers were prepared by Sonogashira coupling of diiodobenzene and bis-acetylene building blocks in the presence of monoacetylene chain terminators. The product mixtures were separated by reverse phase preparative high-pressure liquid chromatography to give a series of pure oligomers up to seven recognition units in length. Duplex formation between length complementary homo-oligomers was demonstrated by 31P NMR denaturation experiments using dimethyl sulfoxide as a competing H-bond acceptor. The denaturation experiments were used to determine the association constants for duplex formation, which increase by nearly 2 orders of magnitude for every phenol-phosphine oxide base-pair added. These experiments show that the phenylacetylene backbone supports formation of extended duplexes with multiple cooperative intermolecular H-bonding interactions, and together with previous studies on the mixed sequence phenylacetylene 2-mer, suggest that this supramolecular architecture is a promising candidate for the development of synthetic information molecules that parallel the properties of nucleic acids.
Saccharide-functionalized organoplatinum(II) metallacycles
Zhou, Fengyan,Li, Shijun,Cook, Timothy R.,He, Zuoli,Stang, Peter J.
, p. 7019 - 7022 (2015/02/19)
Coordination-driven self-assembly can be used to construct metallacycles decorated with saccharide functionalities by combining organoplatinum acceptor building blocks with glycosylated dipyridyl donors. We describe here the synthesis of a suite of donors
Coordination-driven self-assembly of cavity-cored multiple crown ether derivatives and poly[2]pseudorotaxanes
Ghosh, Koushik,Yang, Hai-Bo,Northrop, Brian H.,Lyndon, Matthew M.,Zheng, Yao-Rong,Muddiman, David C.,Stang, Peter J.
, p. 5320 - 5334 (2008/12/20)
The synthesis of a new 120° diplatinum(II) acceptor unit and the self-assembly of a series of two-dimensional metallacyclic polypseudorotaxanes that utilize both metal-ligand and crown ether-dialkyl-ammonium noncovalent interactions are described. Judiciously combining complementary diplatinum(II) acceptors with bispyridyl donor building blocks, with an acceptor and/or donor possessing a pendant dibenzo[24]crown-8 (DB24C8) moiety, allows for the formation of three new rhomboidal bis-DB24C8, one new hexagonal tris-DB24C8, and four new hexakis-DB24C8 metallacyclic polygons in quantitative yields. The size and shape of each assembly, as well as the location and stoichiometry of the DB24C8 macrocycle, can be precisely controlled. Each polygon is able to complex two, three, or six dibenzylammonium ions without disrupting the underlying metallacyclic polygons, thus producing eight different poly[2]pseudorotaxanes and demonstrating the utility and scope of this orthogonal self-assembly technique. The assemblies are characterized with one-dimensional multinuclear (1H and 31P) and two-dimensional (1H- 1H COSY and NOESY) NMR spectroscopy as well as mass spectrometry (ESI-MS). Further analysis of the size and shape of each assembly is obtained through molecular force-field simulations. 1H NMR titration experiments are used to establish thermodynamic binding constants and poly[2]pseudorotaxane/dibenzylammonium stoichiometries. Factors influencing the efficiency of poly[2]pseudorotaxane formation are discussed.
Synthesis, optical, and electrochemical properties of a new family of dendritic oligothiophenes
Zhang, Yong,Zhao, Chunchang,Yang, Jinhua,Kapiamba, Mbiya,Haze, Olesya,Rothberg, Lewis J.,Ng, Man-Kit
, p. 9475 - 9483 (2007/10/03)
(Figure Presented) A new class of semi-flexible dendrimers with oligothiophene (OT) arms up to the third generation have been synthesized and investigated. The synthetic methods employed include a combination of palladium-catalyzed Stille cross-coupling reactions for oligothiophenes, Sonogashira cross-coupling reactions for building blocks, and carbodiimide-mediated esterification for building up the various dendrimers. The optical and electrochemical properties of this series of oligothiophenes-based dendrimers are shown to be strongly influenced by their morphologies as demonstrated by their pronounced solvatochromic and thermochromic responses under different environmental conditions. Introducing rigid oligothiophene arms to shape non-persistent ester-linked dendrimers causes higher generation dendrimers (G2 and G3) to exhibit solvatochromism and thermochromism, while their oligomeric counterpart (3b) and lower generation (G1) analogue do not. Spectroscopic changes due to both intramolecular and intermolecular aggregations are observed.
Synthesis and optical properties of unsymmetrical conjugated dendrimers focally anchored with perylenes in different geometries
Pan, Yongchun,Lu, Meng,Peng, Zhonghua,Melinger, Joseph S.
, p. 6952 - 6958 (2007/10/03)
Two sets of light-harvesting monodendrons with unsymmetrical conjugated phenylacetylene branches and perylene cores, one with π-conjugation from the branches to the core and one without, were synthesized and their photophysical properties were studied by
