cas 75867-39-9, 4-((Trimethylsilyl)ethynyl)aniline

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Photogenerated charge collection on diamond electrodes with covalently linked chromophore monolayers
Encouraged by its rich surface chemistry and excellent electrochemical properties, boron-doped nanocrystalline diamond (B:NCD) is a promising p-type photoelectrode in dye-sensitized solar cells. One method of diamond surface functionalization using stable carbon-carbon bonds involves the electrochemical grafting of diazonium salts. However, this method typically leads to multilayers that may complicate the transport of photogenerated charges. Here, we establish functionalization of B:NCD electrodes by a monolayer of ethynylphenyl molecules using sterically hindered 4-(trimethylsilyl)ethynylbenzenediazonium tetrafluoroborate. Both the density and structural orientation of the grafted layer are investigated by angular resolved X-ray photoelectron spectroscopy, confirming the presence of covalently grafted monolayers. After removal of the trimethylsilyl protective groups, the resulting ethynyl functionalities are employed to immobilize organic donor-acceptor chromophores via Sonogashira cross-coupling reactions. Homogenous surface coverage is achieved even on the B:NCD electrode. Atomic scale DFT computing reveals that for the chromophore with the strongest acceptor unit, efficient charge separation of 20 ? is obtained where photogenerated holes move directly into diamond. Yet, photocurrent and photovoltage measurements suggest competitive electron recombination to the diamond electrode via the redox electrolyte. Correlation between the density of the molecular layer and photocurrents/photovoltage provides better understanding of the charge generation and recombination pathways in diamond-organic photoelectrochemical cells.
Artemenko, A.,Cermák, J.,Haenen, K.,Kavan, L.,Kromka, A.,Krysova, H.,Lopez-Carballeira, D.,Maes, W.,Nicley, S. S.,Raymakers, J.,Rezek, B.,Verstraeten, F.
(2020)
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Synthesis, characterization, photophysics, and anion binding properties of gold(i) acetylide complexes with amide groups
A series of mononuclear gold(i) acetylide complexes with amide groups, Ph3PAuCCC6H4NHC(O)C6H4-R-4 (R = NO2 (3a), CF3 (3b), H (3c), and OMe (3d)), has been synthesized and characterized. The crystal structure of Ph3PAuCCC6H4NHC(O)C6H4-NO2-4 (3a) was determined by X-ray diffraction. The photophysical properties of gold(i) acetylide complexes 3b-3d were studied and the complexes show luminescence both in the solid state and in degassed THF solutions at 298 K. The anion-binding abilities of complexes 3a-3d in CDCl3 were also studied through 1H NMR titration experiments. They show similar anion selectivity trends and 3a exhibits the highest binding affinity towards anions due to the strongest electron-withdrawing ability of the NO2 group. In DMSO, 3a shows a dramatic color change upon addition of F-, which provides access to naked eye detection of F-. This journal is
Shi, Hua-Yun,Qi, Jie,Zhao, Zhen-Ze,Feng, Wen-Juan,Li, Yu-Hao,Sun, Lu,Lin, Zhuo-Jia,Chao, Hsiu-Yi
p. 6168 - 6175
(2014)
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Liquid crystal compound containing butadiyne structure and liquid crystal composition and application thereof
The invention relates to a liquid crystal compound containing a butadiyne structure. The liquid crystal compound is represented by a general formula I. The invention also relates to a liquid crystal composition which at least comprises the compound repres
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(2021/05/08)

Development of a Pre-assembled Through-Bond Energy Transfer (TBET) Fluorescent Probe for Ratiometric Sensing of Anticancer Platinum(ll) Complexes
Fluorescence microscopy has emerged as an attractive technique to probe the intracellular processing of Pt-based anticancer compounds. Herein, we reported the first through-bond energy transfer (TBET) fluorescent probe NPR1 designed for sensitive detectio
Ang, Wee Han,Ong, Jun Xiang
(2020/04/02)

Synthesis and photophysical properties of multilayer emitting π-p-π fluorophores
Fluorescence is widely used in biology, medicine, and analytical chemistry. The anthracene framework has received considerable attention for the luminescent molecular design as an attractive building unit. Herein, Luminescent “π-p-π” anthracene crystals with different multilayer stacking modes were conducted by experimental methods and theoretical calculations. It was found that “these anthracene derivatives showed strong fluorescence and stability in both solution and solid-state; A face-to-face π-π stacking arrangement dominated in N9,N10-diphenyl-2,6-bis((trimethylsilyl)ethynyl)anthracene-9,10-diamine (4), while C/N–H … π interactions were observed in the crystal lattice of 2,6-diethynyl-N9,N10-diphenylanthracene-9,10-diamine (5); The excitation processes of S0→S1 of 4 and 5 belonged to Localized Excitation; The number of photons emitted could be nearly equal to the number of photons absorbed below 120K”. This study is expected to assist in the design of photonic materials in the field of optical chemistry.
Wang, Xiaorong,Zhao, Sanxiao,Chen, Yin,Wang, Jingang
(2019/11/02)

Synthesis and asymmetric catalytic performance of one-handed helical poly(phenylacetylene)s bearing proline dipeptide pendants
One-handed helical substituted polyacetylene has received extensive attention due to its potential in chiral stationary phases and molecular recognition. Here, three one-handed helical poly(phenylacetylene)s bearing proline or proline dipeptide as the pen
Liu, Lijia,Wang, Yaodong,Wang, Fuqingyun,Zhang, Chunhong,Zhou, Yanli,Zhou, Zhengjin,Liu, Xudong,Zhu, Ruiqi,Dong, Hongxing,Satoh, Toshifumi
(2019/11/14)

Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents
Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.
Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen
p. 6765 - 6784
(2019/08/20)

Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines
Transition metal-free radical arylation of heteroarenes is achieved at room temperature by simply adding aqueous sodium carbonate to a solution of the corresponding heteroarene and arenediazonium salt, which can even be formed in situ. Such an easy, inexpensive and mild methodology has been optimized and applied to the expeditious modification of interesting molecular cores like naphthylimide or bisthienylcyclopentenes.
Monzón, Diego M.,Santos, Tanausú,Pinacho-Crisóstomo,Martín, Víctor S.,Carrillo, Romen
p. 325 - 333
(2018/01/15)

Palladium catalysed regio- and stereoselective synthesis of (E)-4-aryl-1,3-bis(trimethylsilyl)but-3-en-1-ynes
A practical and general synthetic approach to a series of 4-aryl-but-3-en-1-ynes is described. In the presence of palladium complexes a variety of aryl bromides (or iodides) undergo coupling with two equivalents of trimethylsilylacetylene with the formati
Rogalski, Szymon,Kubicki, Maciej,Pietraszuk, Cezary
p. 6192 - 6198
(2018/09/17)

Stabilization of High Oxidation State Upconversion Nanoparticles by N-Heterocyclic Carbenes
The stabilization of high oxidation state nanoparticles by N-heterocyclic carbenes is reported. Such nanoparticles represent an important subset in the field of nanoparticles, with different and more challenging requirements for suitable ligands compared to elemental metal nanoparticles. N-Heterocyclic carbene coated NaYF4:Yb,Tm upconversion nanoparticles were synthesized by a ligand-exchange reaction from a well-defined precursor. This new photoactive material was characterized in detail and employed in the activation of photoresponsive molecules by low-intensity near-infrared light (λ=980 nm).
M?ller, Nadja,Rühling, Andreas,Lamping, Sebastian,Hellwig, Tim,Fallnich, Carsten,Ravoo, Bart Jan,Glorius, Frank
supporting information
p. 4356 - 4360
(2017/04/03)

Catalyst-free hydrochlorination protocol for terminal arylalkynes with hydrogen chloride
We present a simple and straightforward protocol for hydrochlorination of terminal arylalkynes to vinyl chlorides using hydrogen chloride under mild reaction conditions. This protocol does not involve any metal catalysts or additives. It is simple, inexpensive, and easy to prepare, and exhibits good reaction activity. The hydrochlorination proceeds smoothly to yield unique regioselective products via the Markovnikov addition rule.
Xu, Cai-Xia,Ma, Cun-Hua,Xiao, Fu-Rong,Chen, Hong-Wei,Dai, Bin
supporting information
p. 1683 - 1685
(2016/11/12)

Pyrimidine or pyridine pyridine ketone compound and its preparation method and application (by machine translation)
The invention discloses a kind of type I of the pyrimidine or pyridine pyridine ketone compound and its preparation and application, which belongs to the technical field of pharmaceutical preparation. The compounds have high-efficient and selectively inhibit the cell cycle dependent kinases (Cdks) CDK4 and CDK6 active, and then by inhibiting CDK4/CDK6 prevent tumor cell division. Therefore, the compounds of this invention can be used for CDK4 and CDK6 the involved in cell cycle control disorders result in various diseases, especially suitable for the treatment of malignant tumors. (by machine translation)
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(2016/10/09)

The design of liquid crystalline bistolane-based materials with extremely high birefringence
We designed three new bistolanes with alkylsulfanyl groups. A symmetric derivative contains short terminal methylsulfanyl groups (-SCH3) on both ends, while two asymmetric derivatives contain a methylsulfanyl group on one end, as well as a highly polarizable cyano (-CN) or isothiocyanate (-NCS) group on the other end. These materials exhibited a well-defined enantiotropic nematic phase, as well as an extremely high birefringence (Δn > 0.6). Most notably, the NCS derivative achieves an extremely high value of 0.77 at 550 nm. These results should be helpful for the design and synthesis of novel nematic materials with high birefringence.
Arakawa, Yuki,Kang, Sungmin,Tsuji, Hideto,Watanabe, Junji,Konishi, Gen-Ichi
p. 92845 - 92851
(2016/10/11)

Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of: O -methoxycarbonylphenylboronic acid with alkynes
Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones in good yields. Excellent regioselectivities were observed, when silyl aryl alkynes were used. The intermediate 3-silyl-2-aryl-substituted indenones were converted to 2,3-diaryl indenones by a three-step protocol involving C-Si bromination and Suzuki-Miyaura coupling reaction.
Ueda, Mitsuhiro,Ueno, Tamami,Suyama, Yuki,Ryu, Ilhyong
supporting information
p. 13237 - 13240
(2016/11/17)

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases
Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.
Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.
supporting information
p. 3013 - 3032
(2015/08/03)

Synthesis of 3-substituted isoindolin-1-ones via a tandem desilylation, cross-coupling, hydroamidation sequence under aqueous phase-transfer conditions
A simple and expedient method for the synthesis of 3-methylene-isoindolin-1-ones 4 under aqueous phase-transfer conditions has been developed. Starting from 2-iodobenzamides 1 and (silyl)alkynes, the products are obtained in high yields and short reaction times (30 min) with the use of inexpensive CuCl/PPh3 catalyst system in the presence of n-Bu4NBr (TBAB) as a phase-transfer agent. Terminal alkynes are conveniently "unmasked" upon in situ desilylation under the reaction conditions. Alkynes possessing heterocyclic moieties were also found as amenable substrates. Furthermore, a one-pot process starting from 2-iodobenzamides 1, aryl halides (bromides or iodides) and trimethylsilylacetylene (TMSA) as a convenient acetylene surrogate was also shown to be feasible under Pd/Cu catalysis.
Munoz, Socrates B.,Aloia, Alexandra N.,Moore, Alexander K.,Papp, Attila,Mathew, Thomas,Fustero, Santos,Olah, George A.,Surya Prakash
supporting information
p. 85 - 92
(2015/12/30)

Tunable electron acceptors based on cyclopenta[hi]aceanthrylenes
A series of substituted cyclopenta[hi]aceanthrylene derivatives with electron donating (NH2, OCH3), neutral (H), and electron withdrawing (COOH, CF3, CN, NO2) substituents were prepared. A room-temperature Sonogashira cross-coupling reaction between 2,7-dibromocyclopenta[hi]aceanthrylene and an appropriately functionalized phenylene ethynylene precursor was utilized to access the materials that were characterized by Nuclear Magnetic Resonance Spectroscopy (NMR), cyclic voltammetry (CV), and UV-Vis spectroscopy. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) were systematically varied when proceeding from electron donating to electron withdrawing substituents. The optical band gap was significantly altered for the most electron donating species, while little change was observed between different electron withdrawing substituents. This study demonstrates the ability to control the frontier orbital energies of this class of cyclopenta-fused polycyclic aromatic hydrocarbon materials through selective substitution.
Zhu, Xinju,Yuan, Bingxin,Plunkett, Kyle N.
supporting information
p. 7105 - 7107
(2015/12/01)

Chemoselective reductions of nitroaromatics in water at room temperature
A robust and green protocol for the reduction of functionalized nitroarenes to the corresponding primary amines has been developed. It relies on inexpensive zinc dust in water containing nanomicelles derived from the commercially available designer surfactant TPGS-750-M. This mild process takes place at room temperature and tolerates a wide range of functionalities. Highly selective reductions can also be achieved in the presence of common protecting groups.
Kelly, Sean M.,Lipshutz, Bruce H.
supporting information
p. 98 - 101
(2014/01/23)

Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes
A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.
Xu, Caixia,Du, Weiyuan,Zeng, Yi,Dai, Bin,Guo, Hao
supporting information
p. 948 - 951
(2014/03/21)

Combined spectroscopic and quantum chemical study of [trans-Ru(C≡CC6H4R1-4)2(dppe)2]n+ and [trans-Ru(C≡CC6H4R1-4)(C≡CC6H4R2-4)(dppe)2]n+ (n = 0, 1) complexes: Interpretations beyond the lowest energy conformer paradigm
The reaction of trans-RuCl(C≡CC6H4R1-4)(dppe)2 (2: R1 = Me (a), C5H11 (b), OMe (c), CO2Me (d), NO2 (e), C≡CSiMe3 (f), C≡CBut (g), NH2 (h)), prepared in situ from reactions of [RuCl(dppe)2]OTf ([1]OTf) with terminal alkynes in CH2Cl2 solutions containing 1,8-diazabicycloundec-7-ene (DBU) and TlBF4, provides a convenient and rapid route to bis(acetylide) complexes trans-Ru(C≡CC6H4R1-4)2(dppe)2 (3a-h) and trans-Ru(C≡ CC6H4R1-4)(C≡CC6H4R2-4)(dppe)2 (4, R1 = C≡CSiMe3, R2 = NH2; 5, R1 = CO2Me, R2 = NH2; 6, R1 = CO2Me, R2 = OMe). However, even in the absence of the chloride abstracting reagent, more strongly electron donating substituents (e.g., R1 = OMe (2c), NH2 (2h)) promote sufficient ionization of the Ru-Cl bond in trans-RuCl(C≡CC6H4R -4)(dppe)2 to lead to slow conversion to bis(alkynyl) complexes 3c,h in the presence of excess alkyne and DBU. Desilylation of 2f and 3f affords 2i and 3i (R1 = C≡CH), respectively. The molecular structures of 3a-d,f-i have been determined and are reported together with the structures of the monoalkynyl complexes 2f,g,i and compared with related compounds from the literature. Complexes 3a-i and 4-6 undergo one reversible electrochemical oxidation process, which can be attributed to depopulation of an orbital with significant alkynyl ligand character. The one-electron-oxidation products [3f]?+, [3h]?+, [4]?+, and [5]?+, chosen to serve as representative examples of this family of complexes, each exhibit a series of NIR absorptions between 15000 and 5000 cm-1 which on the basis of TDDFT calculations cannot be attributed to a single, static lowest energy molecular structure. Rather, the transitions that are responsible for the absorption band envelope have varying degrees of LMCT and inter-alkynyl ligand IVCT or MLCT character that depend not only on the nature of the Rn groups but also on the ensemble of thermally populated molecular conformers in solution with various relative orientations of the metal fragment and arylethynyl moieties. (Figure Presented)
Marqués-González, Santiago,Parthey, Matthias,Yufit, Dmitry S.,Howard, Judith A.K.,Kaupp, Martin,Low, Paul J.
supporting information
p. 4947 - 4963
(2015/04/27)

Bimetallic nano-Pd/PdO/Cu system as a highly effective catalyst for the Sonogashira reaction
A copper-supported nanopalladium catalyst obtained by an innovative method of nanoparticle transfer from the intermediate carrier SiO2 to the target Cu carrier was a highly efficient and selective catalyst, giving as much as quantitative conver
Korzec, Mateusz,Bartczak, Piotr,Niemczyk, Anna,Szade, Jacek,Kapkowski, Maciej,Zenderowska, Paulina,Balin, Katarzyna,Lelatko, Jozef,Polanski, Jaroslaw
p. 1 - 8
(2014/04/03)

Off-rate screening (ORS) by surface plasmon resonance. An efficient method to kinetically sample hit to lead chemical space from unpurified reaction products
The dissociation rate constant kd (off-rate) is the component of ligand-protein binding with the most significant potential to enhance compound potency. Here we provide theoretical and empirical data to show that this parameter can be determined accurately from unpurified reaction products containing designed test compounds. This screening protocol is amenable to parallel chemistry, provides efficiencies of time and materials, and complements existing methodologies for the hit-to-lead phase in fragment-based drug discovery.
Murray, James B.,Roughley, Stephen D.,Matassova, Natalia,Brough, Paul A.
supporting information
p. 2845 - 2850
(2014/05/06)

Cooperative self-assembly of platinum(ii) acetylide complexes
Rod-like platinum(ii) acetylide complexes have been demonstrated to form one-dimensional helical supramolecular polymers by the cooperative growth mechanism, leading to supramolecular gels by bundling single fibrils into entangled networks.
Tian, Yu-Jing,Meijer,Wang, Feng
supporting information
p. 9197 - 9199
(2013/09/24)

Simplifying the conductance profiles of molecular junctions: The use of the trimethylsilylethynyl moiety as a molecule-gold contact
Conductance across a metal|molecule|metal junction is strongly influenced by the molecule-substrate contacts, and for a given molecular structure, multiple conductance values are frequently observed and ascribed to distinct binding modes of the contact at each of the molecular termini. Conjugated molecules containing a trimethylsilylethynyl terminus, -C≡CSiMe 3 give exclusively a single conductance value in I(s) measurements on gold substrates, the value of which is similar to that observed for the same molecular backbone with thiol and amine based contacting groups when bound to under-coordinated surface sites.
Marques-Gonzalez, Santiago,Yufit, Dmitry S.,Howard, Judith A.K.,Martin, Santiago,Osorio, Henrry M.,Garcia-Suarez, Victor M.,Nichols, Richard J.,Higgins, Simon J.,Cea, Pilar,Low, Paul J.
supporting information
p. 338 - 341
(2013/03/14)

Nanostructured monolayers on carbon substrates prepared by electrografting of protected aryldiazonium salts
The electrogeneration of aryl radicals from protected diazonium salts combined with protection-deprotection steps was evaluated to design functional monolayers on carbon substrates with a well-controlled organization at the nanometric scale. The structure
Leroux, Yann R.,Hapiot, Philippe
p. 489 - 495
(2013/05/08)

Copper-promoted sandmeyer trifluoromethylation reaction
A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.
Dai, Jian-Jun,Fang, Chi,Xiao, Bin,Yi, Jun,Xu, Jun,Liu, Zhao-Jing,Lu, Xi,Liu, Lei,Fu, Yao
supporting information
p. 8436 - 8439
(2013/07/19)

A fluorescent color/intensity changed chemosensor for Fe3+ by photo-induced electron transfer (PET) inhibition of fluoranthene derivative
A fluorescent color/intensity changed fluoranthene derivative chemosensor for Fe3+ has been prepared and confirmed by 1H-NMR, 13C-NMR, HRMS, and crystal data, which displays a high selectivity and antidisturbance for Fesu
Li, Zhanxian,Zhang, Lifeng,Li, Xiaoya,Guo, Yongkai,Ni, Zhonghai,Chen, Jianhong,Wei, Liuhe,Yu, Mingming
experimental part
p. 60 - 65
(2012/03/26)

Specific interaction modes in the crystal structures of oligofluorinated tolanes featuring additional electron donor and acceptor groups
A series of partially fluorinated and specifically para-substituted tolanes (1-4) have been synthesized via palladium-catalyzed Sonogashira cross-coupling reaction. The single-crystal structures have been determined by X-ray diffraction. The molecules ado
Stein, Mario,Berger, Ricarda,Seichter, Wilhelm,Hulliger, Jürg,Weber, Edwin
scheme or table
p. 231 - 239
(2012/04/04)

An off-on fluorescent chemosensor of selectivity to Cr3+ and its application to MCF-7 cells
A 'switching-on' fluorescent chemosensor for the selective and sensitive signaling of intraceullar Cr3+ has been designed and synthesized exploiting the guest-induced prohibition of the photoinduced electron transfer process between naphthyridi
Li, Zhanxian,Zhao, Wanying,Zhang, Yuna,Zhang, Lifeng,Yu, Mingming,Liu, Jinxia,Zhang, Hongyan
experimental part
p. 7096 - 7100
(2011/10/05)

A study on the electro-oxidation and electropolymerization of a new OPE linear molecule by EQCM and in situ FTIR spectroelectrochemistry
A novel symmetric conjugated oligo(phenylene-ethynylene) (OPE) linear molecule (1,4-bis(4-aminophenylethynyl)benzene); BAB) was synthesized by Sonogashira cross-coupling reactions. The structure and purity of the compound were confirmed by 1H N
Luo, Jiao,Liu, Meiling,Zhao, Qiangqin,Zhao, Jie,Zhang, Youyu,Tan, Liang,Tang, Hao,Xie, Qingji,Li, Haitao,Yao, Shouzhuo
experimental part
p. 454 - 462
(2011/03/16)

5-(Dimethylamino)-N-(4-ethynylphenyl)-1-naphthalenesulfonamide as a novel bifunctional antitumor agent and two-photon induced bio-imaging probe
A novel compound, (5-(dimethylamino)-N-(4-ethynylphenyl)-1- naphthalenesulfonamide), was prepared and characterized; it shows dual functional roles as an effective antitumor and a two-photon induced bio-imaging agent.
Chui,Wang,Chow,Yuen,Wong,Kwok,Cheng,Wong,Tong,Chan,Lau,Lai,Lam,Fabbri,Tao,Gambari,Wong
supporting information; experimental part
p. 3538 - 3540
(2010/08/07)

Functionalization of multilayer fullerenes (carbon nano-onions) using diazonium compounds and "click" chemistry
(Figure Presented) A novel versatile approach for the functionalization of multilayer fullerenes (carbon nano-onlons) has been developed, which involves the facile introduction of a variety of simple functionalities onto their surface by treatment with In
Flavin, Kevin,Chaur, Manuel N.,Echegoyen, Luis,Giordani, Silvia
supporting information; experimental part
p. 840 - 843
(2010/04/06)

Synthesis of functionalized triazatriangulenes for application in photo- Switchable self-assembled monolayers
Various triazatriangulenes are synthesized by nucleophilic attack at the central C atom of triazatriangulenium ions. The molecular functions, especially azobenzenes, are fixed via an ethynyl linker by in situ deprotection of trimethylsilylalkynes. The structure of two of these molecules is further investigated by X-ray crystallography. The photo-inducedtrans/cis-isomerization of the azobenzene substituted derivatives is analyzed in solution and shows great promise for the preparation of switchable functionalized monolayers, as the triazatriangulenes are known for their self-assembly on gold surfaces. [1].
Kubitschke, Jens,Naether, Christian,Herges, Rainer
scheme or table
p. 5041 - 5055
(2010/11/05)

The sequential Sonogashira-click reaction: A versatile route to 4-aryl-1,2,3-triazoles
Aryl halides can be easily transformed in a one-pot procedure into 4-aryl-1,2,3-triazoles with palladium/copper-catalyzed Sonogashira-click reaction sequence, using trimethylsilylacetylene as acetylene surrogate.
Loerincz, Krisztian,Kele, Peter,Novak, Zoltan
experimental part
p. 3527 - 3532
(2010/02/28)

Linear free-energy correlation analysis of the electronic effects of the substituents in the Sonogashira coupling reaction
Relative rate constants (krel) for the Sonogashira coupling were determined in competitive reactions between iodobenzene and a series of para- and meta-substituted iodobenzenes and compared to the charge on iodine and the z-component of the qua
Gottardo, Christine,Kraft, Thomas M.,Hossain, M. Selim,Zawada, Peter V.,Muchall, Heidi M.
p. 410 - 415
(2008/09/20)

LIGHT EMITTING MOLECULES AND ORGANIC LIGHT EMITTING DEVICES INCLUDING LIGHT EMITTING MOLECULES
Light emitting molecules and organic light emitting devices comprising such light emitting molecules are described. In one embodiment, a light emitting molecule comprises an anchoring group and a charge transport group having a first end and a second end.
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(2008/06/13)

Helical arrays of pendant fullerenes on optically active poly(phenylacetylene)s
Novel, optically active, stereoregular poly(phenylacetylene)s bearing the bulky fullerene as the pendant were synthesized by copolymerization of an achiral phenylacetylene bearing a [60]fullerene unit with optically active phenylacetylene components in th
Nishimura, Tatsuya,Maeda, Katsuhiro,Ohsawa, Sousuke,Yashima, Eiji
p. 1181 - 1190
(2007/10/03)

Sonogashira coupling with aqueous ammonia directed to the synthesis of azotolane derivatives
Sonogashira coupling with aqueous ammonia is tolerable for the reaction of aryl iodides or terminal alkynes bearing an azobenzene group. The reaction of (4-heptyloxyphenyl)ethyne with (4-heptyloxyphenyl)-(4-iodophenyl)diazene in the presence of 1 mol% of
Mohamed Ahmed, Mohamed S.,Mori, Atsunori
p. 9977 - 9982
(2007/10/03)

An approach to long and unsubstituted molecular wires: Synthesis of redox-active, cationic phenylethynyl oligomers designed for self-assembled monolayers
Various oligo(phenyleneethynylene)s (OPEs) have been synthesized in the past, as they are considered as prototypes of molecular wires. When the oligomers are capped by a redox site at one end and a thiol at the other end, the resulting molecules can be grafted as a self-assembled monolayer on a gold electrode and fully studied by electrochemical techniques. Unfortunately, such molecules are usually poorly soluble and require the incorporation of solubilizing pendant groups. In this paper, we show that the replacement of the classically used redox group ferrocene by a cationic organometallic ruthenium complex, namely, [Ru(bipy)2(ppH)]+ (bipy, 2,2′-bipyridine; ppH, 2-(2′-yl-phenyl)pyridine), allows a concise synthesis of an unsubstituted thioacetate-capped OPE up to four repetitive units long. The positive charge does not interfere with the conventional organic chemistry used to elongate, purify, or characterize the hexafluorophosphate salts of the molecules. To our knowledge, this represents the first family of long, poorly substituted OPEs designed for self-assembly.
Hortholary, Cedric,Coudret, Christophe
p. 2167 - 2174
(2007/10/03)

Limits of delocalization in through-conjugated dinitrenes: Aromatization or bond formation?
(Matrix presented) Dinitrenes 4 and 5 both can form quinonoidal structures by conjugative bond formation. However, ESR spectroscopy detects a thermally populated, excited-state, triplet quinonoidal structure only for 4, with a zero-field splitting of |D/hc| = 0.0822 cm-1, |E/hc| ? 0.0 cm-1. The tendency to maintain aromaticity in the additional ring of 5 favors a dinitrene structure (with one less formal π-bond) over a quinonoidal structure. The thermally populated quintet state of 5 has a zero-field splitting of |D/hc| = 0.287 cm-1, |E/hc| ≤ 0.002 c m-1.
Serwinski, Paul R.,Lahti, Paul M.
p. 2099 - 2102
(2007/10/03)

Palladium-catalyzed carbon-carbon coupling reactions using aryl Grignards
Coupling reactions using Pd(PPh3)4 were investigated with a number of electron donating and electron withdrawing substituents. High yields were obtained with both types of substituents. In competitive reactions the electron-withdrawi
Gottardo, Christine,Aguirre, Andrea
p. 7091 - 7094
(2007/10/03)

Combinatorial synthesis of oligo(phenylene ethynylene)s
The combinatorial synthesis of oligo(phenylene ethynylene) tetramers, both in solution and on solid support, is described. These products are of interest for molecular electronics applications. An iterative sequence, coupling of aryl halides to alkynes under Sonogashira conditions, was used. Five monomers functionalized with electron-donating or electron-withdrawing groups were synthesized, and used to generate a library of 25 trimers in a solution-phase based process. A library of 24 tetramers was prepared by subsequent protodesilylation and coupling with the alligator clip 4-iodo-1-thioacetylbenzene. The solution-phase based sequence was successfully adapted to a higher yielding directed split-and-pool solid-phase process, with average yields of 78-86% for each step over seven steps. A triazene linker group was used to attach the starting monomer to the polymer beads. At the completion of the solid-phase-based process, traceless cleavage of trimers from the resin was achieved by sonication of the resin in 10% HCl/THF solution. The released products were then poised for the final step in the sequence, attachment of the alligator clip.
Hwang, Jiunn-Jye,Tour, James M.
p. 10387 - 10405
(2007/10/03)

Rapid homogeneous-phase sonogashira coupling reactions using controlled microwave heating
A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with t
Erdelyi,Gogoll
p. 4165 - 4169
(2007/10/03)

Tetrahedral onsager crosses for solubility improvement and crystallization bypass
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.
Aujard,Baltaze,Baudin,Cogne,Ferrage,Jullien,Perez,Prevost,Lin Mao Qian,Ruel
p. 8177 - 8188
(2007/10/03)

Phenylene ethynylene pentamers for organic electroluminescence
An isomeric family of eighteen triisopropylsilyl-capped phenylene ethynylene pentamers (molecular formula C60H62Si2) has been prepared by using fast parallel synthesis, for organic electroluminescence. Each pentamer was grown on a polymer support of propylaminomethylated polystyrene by using a series of palladium-catalysed reactions between aryl iodides and alkynes. "Tea bag" technology was used to carry out several different reactions simultaneously in the same flask. Here I present the syntheses of the materials, compare their photoluminescence both in solution and in the solid state (amorphous thin films) and describe the incorporation of the most promising pentamer into organic electroluminescence devices.
Anderson
p. 4706 - 4714
(2007/10/03)

Phenylene ethynylene diazonium salts as potential self-assembling molecular devices
(matrix presented) Functionalized diazonium salts for molecular electronic devices are prepared by the reaction of the corresponding anilines with NOBF4 in sulfolane-acetonitrile solvent.
Kosynkin, Dmitry V.,Tour, James M.
p. 993 - 995
(2007/10/03)

Novel synthetic route to allyl cyanamides: Palladium-catalyzed coupling of isocyanides, allyl carbonate, and trimethylsilyl azide [6]
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Kamijo,Jin,Yamamoto
p. 9453 - 9454
(2007/10/03)

Synthesis and preliminary testing of molecular wires and devices
Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
p. 5118 - 5134
(2007/10/03)

Unprecedented cesium and potassium fluorides catalyzed trialkylsilylation and tributylstannylation of terminal alkynes with trifluoromethyl-trialkylsilanes and -tributylstannane
Cesium and potassium fluorides promoted trialkylsilylation and tributylstannylation of terminal alkynes with trifluoromethyl-trialkylsilanes and -tributylstannane were found to give 1-silyl- and 1-tributylatannyl-alkynes in high yield. The present reactions are applicable to 1-alkynes having a wide range of functional groups such as acetal, iodo, silyl, amino, amido and carbonyl (except for aldehyde) groups. (C) 2000 Elsevier Science Ltd.
Ishizaki, Miyuki,Hoshino, Osamu
p. 8813 - 8819
(2007/10/03)

Sequential catalytic synthesis of rod-like conjugated poly-ynes
Several poly-ynes X-[C ≡ C-C6H4-](n)C ≡ C-Si(i)Pr3 (X = H, SiMe3) with controlled length (n = 1, 2, 3, 4) have been prepared from the easily accessible 4-trimethylsilylethynyl iodobenzene by using iterative and convergent methods based on both Pd/Cu catalysed C-C cross-coupling and selective desilylation reactions.
Lavastre, Olivier,Ollivier, Laurence,Dixneuf, Pierre H.,Sibandhit, Sourisak
p. 5495 - 5504
(2007/10/03)