- Pushing fullerene absorption into the near-IR region by conjugately fusing oligothiophenes
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Fusing two in one: The π-electron systems of fullerene and an oligothiophene were conjugately fused by an open-cage process. This led to novel fullerene-oligothiophene chromophores with significantly enhanced light-absorbing capability, which covers a wid
- Xiao, Zuo,Ye, Gang,Liu, Ying,Chen, Shan,Peng, Qian,Zuo, Qiqun,Ding, Liming
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Read Online
- Organic NIR-II dyes with ultralong circulation persistence for image-guided delivery and therapy
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Nanocarriers hold great promise for the controlled release of therapeutic payloads to target organs/tissues and extended duration of anticancer agents in the bloodstream. However, limited data on their in vivo pharmacokinetics and delivery process hamper clinical applications. Here we report a series of micellar nanocarriers self-assembled from new-generation thiophenthiadiazole (TTD)-based NIR-II fluorophores HLAnP (n = 1–4) for simultaneous bioimaging and drug delivery. The NIR-II HLA4P nanocarrier displays exceptional non-fouling performance, minimal immunogenicity, ultralong blood half-life, and high tumor accumulation even with different administration routes. When used as a drug carrier, HLA4P with encapsulated doxorubicin (DOX) realized accurate tumor targeting and continuous real-time in vivo NIR-II tracking of drug delivery and therapy, showing a sustained release rate, improved therapeutic effect, and diminished cardiotoxicity as compared to free DOX. This study provides a new perspective on the design of dual-functional NIR-II fluorophores for diagnostic and therapeutic applications.
- Li, Yang,Gao, Jianfeng,Wang, Shuping,Li, Shijun,Hou, Xiaowen,Pan, Yanna,Gao, Jialu,Qiao, Xue,Tian, Zhiquan,Chen, Deliang,Deng, Hai,Deng, Zixin,Hong, Xuechuan,Xiao, Yuling
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p. 157 - 169
(2022/01/14)
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- Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold
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The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The 13C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142.1 ppm (Molsidomine carbene) and δ = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions.
- Freese, Tyll,Lücke, Ana-Luiza,Schmidt, Catharina A.S.,Polamo, Mika,Nieger, Martin,Namyslo, Jan C.,Schmidt, Andreas
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p. 5350 - 5357
(2017/08/11)
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- DEVICE FOR REGULATING THE PASSAGE OF ENERGY
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The present application relates to a device for regulating the passage of energy from an outside space into an inside space, to compounds, windows and uses of the devices and compounds.
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Paragraph 0193-0195
(2017/09/29)
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- Highly π-extended polymers based on phenanthro-pyrazine: Synthesis, characterization, theoretical calculation and photovoltaic properties
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Two novel narrow bandgap conjugated polymers containing phenanthro-pyrazine unit have been successfully synthesized by the Stille coupling reaction. Comparing to the common polymers containing dithiophen-quinoxaline or dithiophen-thieno[3,4-b]pyrazine moi
- Wang, Zhiming,Gao, Zhao,Feng, Ying,Liu, Yulong,Yang, Bing,Liu, Dandan,Lv, Ying,Lu, Ping,Ma, Yuguang
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p. 6191 - 6199
(2013/10/22)
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- Synthesis and characterization of thieno[3,4- b ]pyrazine-based terthienyls: Tunable precursors for low band gap conjugated materials
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Synthetic methods have been developed for the preparation of new 2,3-dihalo- and 2,3-ditriflato-5,7-bis(2-thienyl)thieno[3,4-b]pyrazines. From these reactive intermediates, a variety of new 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines hav
- Schwiderski, Ryan L.,Rasmussen, Seth C.
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p. 5453 - 5462
(2013/07/26)
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- Dual functions of a novel low-gap polymer for near infra-red photovoltaics and light-emitting diodes
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We have synthesised and characterised a new low-gap conjugated polymer, with a broad absorption profile. In blends with a C70 derivative we demonstrate power conversion efficiencies of 0.76%. We show electroluminescence from the polymer peaking at 956 nm, and quantum efficiency of 0.02% in a blend.
- Li, Penglei,Fenwick, Oliver,Yilmaz, Seyfullah,Breusov, Dietrich,Caruana, Daren J.,Allard, Sybille,Scherf, Ullrich,Cacialli, Franco
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supporting information; experimental part
p. 8820 - 8822
(2011/09/21)
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- Low band gap conjugated small molecules containing benzobisthiadiazole and thienothiadiazole central units: Synthesis and application for bulk heterojunction solar cells
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Two novel conjugated low band gap small molecules (SMs), M1 and M2, containing benzobisthiadiazole and thienothiadiazole central units, respectively, were synthesized. Both SMs carried terminal cyanovinylene 4-nitrophenyl at both sides which were connected to the central unit with a thiophene ring. The long-wavelength absorption band was located at 591-643 nm and the optical band gap was 1.62-1.63 eV, which is lower than that of P3HT. These two SMs were investigated as electron donor materials along with PCBM or F as electron acceptors for fabrication of bulk heterojunction (BHJ) organic photovoltaic devices. F is a modified PCBM which has been previously synthesized and used as an electron acceptor for poly(3-hexylthiophene) (P3HT). The power conversion efficiency (PCE) for M1:PCBM, M1:F, M2:PCBM and M2:F was 1.05%, 2.02%, 1.23% and 2.72%, respectively. The higher PCE for the devices with M2 as the electron donor has been related to the improved hole mobility for M2. However, the improved PCE for the devices with F as the electron acceptor has been attributed to the more intense absorption of F in the visible region than that of PCBM and also to the higher open circuit voltage resulting from the higher LUMO level of F. We have also fabricated devices with M2:F cast film from mixed solvents. The PCE for the BHJ devices with the as cast and thermally annealed M2:F (mixed solvents) is 3.34% and 3.65%, respectively.
- Mikroyannidis,Tsagkournos,Sharma,Vijay,Sharma
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scheme or table
p. 4679 - 4688
(2011/10/13)
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- New azaborine-thiophene heteroacenes
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A new class of heteroacenes containing B, N and S elements in the 22-electron aromatic nucleus has been synthesized by reaction of diaminoterthiophenes with dichlorophenylborane. Their structure was studied by X-ray crystallography and DFT calculations. UV-Vis absorption /emission spectroscopy shows high rigidity and deep-blue fluorescence of these compounds.
- Lepeltier, Marc,Lukoyanova, Olena,Jacobson, Alex,Jeeva, Shehzad,Perepichka, Dmitrii F.
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supporting information; experimental part
p. 7007 - 7009
(2010/11/16)
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- Low-band gap copolymers containing thienothiadiazole units: Synthesis, optical, and electrochemical properties
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Novel low-band gap alternating copolymers consisting of 9,9-bis(2-ethylhexyl)fluorene and 4,6-di(2-thienyl)thieno[3,4-c][1,2,5] thiadiazole and its 3,3″-dialkyl derivatives were synthesized by Suzuki copolymerization reaction, and their photophysical and electrochemical properties were studied. The copolymers possess small optical band gap 1.3-1.4 eV. The absorption covers the whole visible spectral region. The long-wavelength absorption maxima in thin films located at approximately 750-785 nm are significantly red shifted compared with those in solution, indicating strong intermolecular interactions. The introduction of alkyl chains to the thiophene units increases the molecular weights of soluble fractions and solubility of the final copolymers, leading to the improved processability of thin films. Polymer solutions exhibited solvatochromism and thermochromism, which is strongly supported by the involvement of the alkyl chains. The copolymers exhibited ambipolar redox properties and reversible electrochromic behavior. The electronic properties are influenced only slightly by alkyl substituents.
- Kminek, Ivan,Vyprachticky, Drahomir,Kriz, Jaroslav,Dybal, Jiri,Cimrova, Vera
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scheme or table
p. 2743 - 2756
(2011/03/19)
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- Iron(II) complexes containing thiophene-substituted "bispicen" ligands Spin-crossover, ligand rearrangements, and ferromagnetic interactions
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The synthesis and characterization of three new tetradentate "bispicen-type" ligands containing a substituted thiophene heterocycle are described [2,5-thienyl substituents = H (7), Ph (8), or 2-thienyl (9)]. Iron(II) bis(thiocyanate) coordination complexe
- Cheng, Haojin,Djukic, Brandon,Jenkins, Hilary,Gorelsky, Serge,Lemaire, Martin
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experimental part
p. 954 - 963
(2011/01/06)
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- Conducting-polymer electrochemical switching as an easy means for control of the molecular properties of grafted transition metal complexes
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Copper(II) 3′,4′-bis(N,N′-oxamato)terthiophene has been synthesized and electropolymerized. The copper(II)-complex centers are not affected by the polymerization process, which involves coupling between Cα carbon atoms of the terthiophene units and leads to a new conjugated polymer consisting of polythiophene chains bearing bis(oxamato)- CuII groups regioregularly grafted onto the polymer backbone. The polymer is stable with respect to polythiophene electroactivity, and no demetallation or modification of the Cu oxidation state occurs over a large potential range. In this material, the two moieties exhibit direct electronic interaction, which makes it possible to use the conductive polymer backbone as a molecular wire or a nanocontact capable of inputting to the bis(oxamato)-CuII groups through the polythiophene-switching reaction. FTIR, XPS, and XAS spectroscopies have been used to study the effect of the state of the conducting polymer upon the properties of the copper(II) center (electron density, ligand field strength, size of cavity, force constants of some bonds). These properties can be controlled to some extent by the potential applied to this device. From the point of view of the copper(II) center, this effect is similar to the grafting of substituents with various electronic properties.
- Mangeney, Claire,Lacroix, Jean-Christophe,Chane-Ching, Kathleen I.,Jouini, Mohamed,Villain, Francoise,Ammar, Souad,Jouini, Nouredine,Lacaze, Pierre-Camille
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p. 5029 - 5040
(2007/10/03)
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- Synthesis of α-Thiophene Oligomers via Organotin Compounds
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A versatile synthetic route involving the use of organotin compounds has been applied for the preparation of functionalized oligothiophenes.Thus, substituted α-bithiophenes have been synthesized via the coupling reaction of 2-bromothiophenes with 2-trimethylstannylthiophene.The latter reagent couples with 2,5-dibromothiophenes to give the α-terthiophenes which are also accessible through the reaction of 5-trimethylstannyl-α-bithiophene with 2-bromothiophenes. 2,5-Bis(trimethylstannyl)thiophene and 5,5'-bis(trimethylstannyl)-α-bithiophene react with 2-bromothiophenes to give α-terthiophenes and α-quaterthiophenes, respectively. α-Quaterthiophene is also produced via the reaction of 5-trimethylstannylthiophene with 5,5'-dibromo-α-bithiophene.The coupling reaction of 5-trimethylstannyl-α-bithiophene with 2,5-dibromothiophene affords the α-quinquethiophene.The structures of the new compounds were confirmed by elemental analysis, Mass spectrometry, 1H- and 13C-NMR spectral data.Keywords: Functionalized α-thiophene oligomers; synthesis; 2-stannylthiophenes
- Kamal, Marwan R.,Al-Taweel, Samir A.,El-Abadelah, Mustafa M.,Ajaj, Khalid M. Abu
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- Synthesis of New Narrow Bandgap Polymers Based on 5,7-Di(2-thienyl)thienopyrazine and its Derivatives
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New narrow bandgap polymers with bandgaps of 1.0-1.5 eV have been synthesized from the title monomers.
- Kitamura, Chitoshi,Tanaka, Shoji,Yamashita, Yoshiro
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p. 1585 - 1586
(2007/10/02)
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