175345-90-1Relevant articles and documents
Synthesis, characterization, and preliminary fluorescence study of a mixed-ligand bis(dicarbollyl)nickel complex bearing a tryptophan-BODIPY FRET couple
Shlyakhtina, Natalia I.,Safronov, Alexander V.,Sevryugina, Yulia V.,Jalisatgi, Satish S.,Hawthorne, M. Frederick
, p. 234 - 244 (2015)
In continuation of our work on nickelacarborane-based nanomolecular devices, the design and synthesis of a bis(dicarbollyl)nickel complex, in both formal Ni(III) and Ni(IV) oxidation states, bearing two fluorophore molecules capable of fluorescence resona
Turn-off mode fluorescent norbornadiene-based photoswitches
Tebikachew, Behabitu Ergette,Edhborg, Fredrik,Kann, Nina,Albinsson, Bo,Moth-Poulsen, Kasper
, p. 23195 - 23201 (2018)
Single-molecule fluorescence emission of certain positive photochromic systems such as diarylethenes have been exploited for biological imaging and optical memory storage applications. However, there is a lack of understanding if negative photochromic sys
Donor–acceptor–acceptor-based non-fullerene acceptors comprising terminal chromen-2-one functionality for efficient bulk-heterojunction devices
Srinivasa Rao, Pedada,Gupta, Akhil,Bhosale, Sidhanath V.,Bilic, Ante,Xiang, Wanchun,Evans, Richard A.,Bhosale, Sheshanath V.
, p. 502 - 511 (2017/07/28)
Two simple semiconducting donor–acceptor–acceptor (D–A1–A) modular, small molecule, non-fullerene electron acceptors, 2-(4-(diphenylamino)phenyl)-3-(4-((2-oxo-2H-chromen-3-yl)ethynyl)phenyl)buta-1,3-diene-1,1,4,4-tetracarbonitrile (P2) and 2-(4-(3,3-dicyano-1-(4-(diphenylamino)phenyl)-2-(4-((2-oxo-2H-chromen-3-yl)ethynyl)phenyl)allylidene)cyclohexa-2,5-dien-1-ylidene)malononitrile (P3), were designed, synthesized and characterized for application in solution-processable bulk-heterojunction solar cells. The optoelectronic and photovoltaic properties of P2 and P3 were directly compared with those of a structural analogue, 3-((4-((4-(diphenylamino)phenyl)ethynyl)phenyl)ethynyl)-2H-chromen-2-one (P1), which was designed based on a D–A format. All of these new materials comprised an electron rich triphenylamine (TPA) donor core (D) and electron deficient chromen-2-one terminal core (A). In the simple D–A system, TPA and chromenone were the terminal functionalities, whereas in the D–A1–A system, tetracyanoethylene (TCNE) and tetracyanoquinodimethane (TCNQ) derived functionalities were incorporated as A1 units by keeping the D/A units constant. The inclusion of A1 was primarily done to induce cross-conjugation within the molecular backbone and hence to generate low band gap targets. The physical and optoelectronic properties were characterized by ultraviolet–visible (UV–Vis), thermogravimetric analysis, photo-electron spectroscopy in air and cyclic voltammetry. These new materials exhibited broadened absorption spectra, for instance panchromatic absorbance in case of P3, excellent solubility and thermal stability, and energy levels matching those of the conventional and routinely used donor polymer poly(3-hexyl thiophene) (P3HT). Solution-processable bulk-heterojunction devices were fabricated with P1, P2 and P3 as non-fullerene electron acceptors. Studies on the photovoltaic properties revealed that the best P3HT: P3-based device showed an impressive enhanced power conversion efficiency of 4.21%, an increase of around two-fold with respect to the efficiency of the best P3HT: P1-based device (2.28%). Our results clearly demonstrate that the D–A1–A type small molecules are promising non-fullerene electron acceptors in the research field of organic solar cells.
Synthesis of Homoditopic Ligands with an Incrementable Rodlike Backbone
Demay-Drouhard, Paul,Chamoreau, Lise-Marie,Guillot, Régis,Policar, Clotilde,Bertrand, Hélène C.
supporting information, p. 131 - 137 (2017/01/14)
We describe the synthesis of architectures that consist of a symmetrical rodlike oligo(phenylene-ethynylene) (OPE) backbone of incrementable length connected to a pair of classical ligands for metal coordination. OPE spacers decorated with various end gro
Magnetic resonance imaging/fluorescence dual modality protocol using designed phosphonate ligands coupled to superparamagnetic iron oxide nanoparticles
Lam, Tina,Avti, Pramod K.,Pouliot, Philippe,Tardif, Jean-Claude,Rhéaume, éric,Lesage, Frederic,Kakkar, Ashok
supporting information, p. 3969 - 3981 (2016/06/13)
A simple and versatile methodology to tailor the surface of superparamagnetic iron oxide nanoparticles (SPIONs), and render additional fluorescence capability to these contrast agents, is reported. The dual modality imaging protocol was developed by designing multi-functional scaffolds with a combination of orthogonal moieties for aqueous dispersion and stealth, to covalently link them to SPIONs, and carry out post-functionalization of nanoparticles. SPIONs stabilized with ligands incorporating surface-anchoring phosphonate groups, ethylene glycol backbone for aqueous dispersion, and free surface exposed OH moieties were coupled to near-infrared dye Cy5.5A. Our results demonstrate that design of multi-tasking ligands with desired combination and spatial distribution of functions provides an ideal platform to construct highly efficient dual imaging probes with balanced magnetic, optical and cell viability properties.
H-aggregates of oligophenyleneethynylene (OPE)-BODIPY systems in water: Guest size-dependent encapsulation mechanism and co-aggregate morphology
Allampally, Naveen Kumar,Florian, Alexander,Mayoral, Maria Jose,Rest, Christina,Stepanenko, Vladimir,Fernandez, Gustavo
supporting information, p. 10669 - 10678 (2014/11/07)
The synthesis of a new oligophenyleneethynylene (OPE)-4,4-difluoro-4-bora- 3a,4a-diaza-s-indacene (BODIPY) bolaamphiphile 1 and its aqueous self-assembly are reported. Compound 1 forms H-type aggregates in aqueous and polar media, as demonstrated by UV/Vis and fluorescence experiments. Concentration-dependent 1H NMR studies in CD3CN reveal that the BODIPY units are arranged on top of each other into π-stacks with H-type excitonic coupling, as supported by ROESY NMR and theoretical calculations and visualized by Cryo-SEM studies. A detailed analysis of the spectral changes observed in temperature-dependent UV/Vis studies reveals that 1 self-assembles in a non-cooperative (isodesmic) fashion in water. The hydrophobic interior of these self-assembled structures can be exploited to encapsulate hydrophobic dyes, such as tetracene and anthracene. Both dyes absorb in a complementary region of the UV/Vis spectrum and are small enough to interact with the hydrophobic segments of 1. Temperature-dependent UV/Vis studies reveal that the spectral changes associated to the encapsulation mechanism of tetracene can be fitted to a Boltzmann function, and the initially flexible fibres of 1 rigidify upon guest addition. In contrast, the co-assembly of 1 and anthracene is a highly cooperative process, which suggests that a different class of (more-ordered) aggregates is formed. TEM and Cryo SEM imaging show the formation of uniform spherical nanoparticles, indicating that a subtle change in the guest molecular structure induces a significant change in the encapsulation mechanism and, consequently, the aggregate morphology. Dye encapsulation: We report the aqueous self-assembly of a new oligophenyleneethynylene (OPE)-BODIPY amphiphilic derivative into H-type aggregates and its ability to encapsulate hydrophobic guest molecules. Subtle changes in the guest size induce a dramatic change of the encapsulation mechanism. Addition of tetracene leads to the non-cooperative formation of stiff fibres, whereas co-assembly with anthracene is a highly cooperative process, leading to highly organized micellar assemblies.
Self-assembly and (hydro)gelation triggered by cooperative π-π And unconventional C-H×××X hydrogen bonding interactions
Rest, Christina,Mayoral, María José,Fucke, Katharina,Schellheimer, Jennifer,Stepanenko, Vladimir,Fernández, Gustavo
supporting information, p. 700 - 705 (2014/01/23)
Weak C-H×××X hydrogen bonds are important stabilizing forces in crystal engineering and anion recognition in solution. In contrast, their quantitative influence on the stabilization of supramolecular polymers or gels has thus far remained unexplored. Herein, we report an oligophenyleneethynylene (OPE)-based amphiphilic PtII complex that forms supramolecular polymeric structures in aqueous and polar media driven by π-π and different weak C-H×××X (X=Cl, O) interactions involving chlorine atoms attached to the PtII centers as well as oxygen atoms and polarized methylene groups belonging to the peripheral glycol chains. A collection of experimental techniques (UV/Vis, 1D and 2D NMR, DLS, AFM, SEM, and X-Ray diffraction) demonstrate that the interplay between different weak noncovalent interactions leads to the cooperative formation of self-assembled structures of high aspect ratio and gels in which the molecular arrangement is maintained in the crystalline state. Growing hand in hand! Multiple unconventional C-H×××X (X=O, Cl) hydrogen-bonding interactions, assisted by π-π interactions, are strong enough to drive the cooperative formation of supramolecular polymers and gels in polar and aqueous media. The aggregates consolidate themselves in the crystals, as shown by combined studies in solution and crystalline state. Copyright
K3PO4-KOH mixture as efficient reagent for the deprotection of 4-aryl-2-methyl-3-butyn-2-ols to terminal acetylenes
Smeyanov, Alexey,Schmidt, Andreas
, p. 2809 - 2816 (2013/08/23)
A mixture of potassium hydroxide and potassium phosphate was found to be an active reagent mixture for the cleavage of 2-hydroxypropyl-protected acetylenes. The reaction was performed in toluene at reflux temperature and gave terminal acetylenes in good to excellent yields within very short periods of time. Numerous other functional groups are tolerated. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for full experimental and spectral details.
Cooperative supramolecular polymerization driven by metallophilic Pd?Pd interactions
Mayoral, María José,Rest, Christina,Stepanenko, Vladimir,Schellheimer, Jennifer,Albuquerque, Rodrigo Q.,Fernández, Gustavo
supporting information, p. 2148 - 2151 (2013/03/28)
A new oligophenyleneethynylene (OPE)-based Pd(II) pyridyl complex has been synthesized, and its self-assembly has been investigated in solution, in the bulk state, and on surfaces. Detailed analysis of concentration- and temperature-dependent UV-vis studies in methylcyclohexane supported by DFT calculations demonstrate for the first time that cooperative supramolecular polymerization processes can be driven by metallophilic interactions.
Glaser coupling at metal surfaces
Gao, Hong-Ying,Wagner, Hendrik,Zhong, Dingyong,Franke, Joern-Holger,Studer, Armido,Fuchs, Harald
supporting information, p. 4024 - 4028 (2013/05/21)
On-surface synthesis is a promising approach for constructing covalently bound nanostructures. However, the number of reliable chemical reactions suitable for on-surface chemistry is very limited. Arylalkynes can be coupled at various surfaces in a novel
