- Proton-template synthesis, structure, and characterization of a Robson- type macrocycle with a totally π-conjugated system
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π-Conjugated (1-4) and partially reduced (5) macrocyclic Schiff bases have been obtained by proton-template condensation of 2,6-diformyl-4-R1- phenol (R1 = Me, t-Bu) with 1,2-diamino-4,5-R2-benzene (R2 = H, Me).
- Tian, Yunqi,Tong, Jian,Frenzen, Gerlinde,Sun, Jin-Yu
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Read Online
- A new copper(II) selective fluorescence probe based on naphthalimide: Synthesis, mechanism and application in living cells
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A new fluorescence probe L based on naphthalimide has been synthesized for selective and quantitative detection of Cu2 + in CH3CN:H2O (4:1, v/v) solution. L exhibited a strong green fluorescence. Upon addition of 2 equiv.
- He, Guangjie,Meng, Qingtao,Zhao, Xiuwen,He, Cheng,Zhou, Peng,Duan, Chunying
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Read Online
- Antioxidant, DNA interaction, molecular docking and cytotoxicity studies of aminoethylpiperazine-containing macrocyclic binuclear copper(II) complexes
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A series of new macrocyclic binuclear copper(II) complexes of the type [Cu2L1–5(ClO4)](ClO4) (1–5) were synthesized by template condensation between precursor compounds 2,6-bis(4-aminoethylpiperazin-1-ylmethyl)-
- Karthick,Karthikeyan,Korrapati, Purna Sai,Rahiman, A. Kalilur
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- Triptycene scaffolds: Synthesis and properties of triptycene-derived Schiff base compounds for the selective and sensitive detection of CN? and Cu2+
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A series of triptycene-derived Schiff bases were synthesized by condensation between amino triptycenes with an appropriate aldehyde and were isolated in good to excellent (85–90%) yields. Amongst these, a triptycene-hydroxybenzaldehyde Schiff base compound proved to be a selective sensor for cyanide. It exhibited a “turn-on” fluorescence response at 490?nm to CN? facilitated by the nucleophilic addition of CN? to the aldehyde group, accompanied by a visible color change from orange to yellow. Likewise, a triptycene salicylaldehyde adduct was shown to be highly sensitive towards the detection of the CN? ion with a detection limit of 0.9?μM. On the other hand a triptycene-BODIPY Schiff base compound could be used for the detection of Cu2+ ions over other competing, biologically relevant metal ions in acetonitrile. Photophysical studies revealed a 1:1 binding model for the triptycene-BODIPY compound.
- Emandi, Ganapathi,Browne, Michelle P.,Lyons, Michael E.,Prior, Caroline,Senge, Mathias O.
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p. 2956 - 2965
(2017/04/26)
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- Preparation method and application of mercaptan fluorescence probe based on coumarin
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The invention discloses a preparation method and application of a mercaptan fluorescence probe based on coumarin. The preparation method includes: coumarin and p-tert-butylphenol dialdehyde are used as raw materials to synthesize a bis-Schiff base coumarin derivative (compound I), the compound I has strong fluorescence, and the compound I is coordinated with copper ions to prepare coumarin-copper ion (II) complex, namely the mercaptan fluorescence probe I-Cu (II). Due to the influence of the paramagnetism of Cu2+ and photoinduction electron transfer effect, the fluorescence of the compound I is quenched; sulfur atoms in compounds such as mercapto-amino acid and derivatives such as glutathione thereof and Cu2+ have a strong coordination effect, the competitive coordination effect allows the copper ions in the coumarin-copper ion (II) complex to be taken away by the mercapto-amino acid and the derivatives thereof so as to regenerate the compound I, and the fluorescence of the compound I is restored. Accordingly, a method for fast and simply detecting mercaptan compounds is built.
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Paragraph 0043; 0044; 0045; 0046;
(2016/12/07)
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- Dinucleating Ligand Platforms Supporting Indium and Zinc Catalysts for Cyclic Ester Polymerization
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The synthesis of the first alkoxide-bridged indium complex supported by a chiral dinucleating ligand platform (1), along with its zinc analogue (2), is reported. Both complexes are synthesized in a one-pot reaction starting from a chiral dinucleating bis(diamino)phenolate ligand platform, sodium ethoxide, and respective metal salts. The dinucleating indium analogue (7) based on an achiral ligand backbone is also reported. Indium complexes bearing either the chiral or achiral ligand catalyze the ring-opening polymerization of racemic lactide (rac-LA) to afford highly heterotactic poly(lactic acid) (PLA; Pr > 0.85). The indium complex bearing an achiral ligand affords essentially atactic PLA from meso-LA. The role of the dinucleating ligand structure in catalyst synthesis and polymerization activity is discussed.
- Kremer, Alexandre B.,Osten, Kimberly M.,Yu, Insun,Ebrahimi, Tannaz,Aluthge, Dinesh C.,Mehrkhodavandi, Parisa
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supporting information
p. 5365 - 5374
(2016/06/14)
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- Meso-Salicylaldehyde substituted BODIPY as a chemodosimetric sensor for cyanide anions
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The meso-salicylaldehyde substituted BODIPY was synthesized over a sequence of steps and characterized by X-ray crystallography, mass, NMR, absorption, fluorescence and electrochemical techniques. The crystal structure showed the presence of strong intram
- Dvivedi, Avanish,Rajakannu, Palanisamy,Ravikanth, Mangalampalli
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p. 4054 - 4062
(2015/04/21)
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- Readily prepared inclusion forming chiral calixsalens
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Calixsalens, chiral triangular hexaimines are readily synthesized by [3 + 3] cyclocondensation of trans-(R,R)-1,2-diaminocyclohexane with 2-hydroxyisophthalaldehyde derivatives. The usually rigid calixsalen ring is able to invert its conformation as a consequence of steric repulsion between bulky substituents at the C5 positions of the aromatic rings. The steric and electronic nature of the substituents does not affect only the conformation of the macrocycle. Small polar substituents enforce dimeric self-association to form an apohost where each of the monomers simultaneously serves as the host and the guest of its partner. Non-associating calixsalens form assemblies in which two symmetry-related molecules are arranged in a head-to-head fashion to form a capsule, or unimolecular cages that are able to entrap solvent molecules in their intrinsic voids.
- Janiak, Agnieszka,Petryk, Ma?gorzata,Barbour, Leonard J.,Kwit, Marcin
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supporting information
p. 669 - 673
(2016/01/12)
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- A highly selective and reversible fluorescent Cu2+ and S2- probe under physiological conditions and in live cells
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A new spiropyran functionalized rhodamine derivative RB-SP2 has been synthesized and applied to detect Cu2+ and S2-. RB-SP2 was then used as an imaging probe for detection of these ions in HeLa cells at the physiological pH. This jou
- Zhou, Quan,Zhu, Yong,Sheng, Pengtao,Wu, Zeming,Cai, Qingyun
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p. 46951 - 46954
(2015/01/08)
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- Selective tracking of lysosomal cu2+ ions using simultaneous target- and location-activated fluorescent nanoprobes
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Levels of lysosomal copper are tightly regulated in the human body. However, few methods for monitoring dynamic changes in copper pools are available, thus limiting the ability to diagnostically assess the influence of copper accumulation on health status. We herein report the development of a dual target and location-activated rhodamine-spiropyran probe, termed Rhod-SP, activated by the presence of lysosomal Cu2+. Rhod-SP contains a proton recognition unit of spiropyran, which provides molecular switching capability, and a latent rhodamine fluorophore for signal transduction. Upon activation by lysosomal acidic pH, Rhod-SP binds with Cu2+ by spiropyran-based proton activation, promoting, in turn, rhodamine ring opening, which shows a "switched on" fluorescence signal. However, to protect Rhod-SP from degradation and interference by the physiological environment, it is engineered on mesoporous silica nanoparticles (MSNs), and the surface of Rhod-SP@MSNs is further anchored with β-cyclodextrin (β-CD) to enhance the solubility and bioavailability of Rhod-SP@MSN-CD. Next, to enhance cell specificity, a guiding unit of c(RGDyK) peptide conjugated adamantane (Ad-RGD) as prototypical system, is incorporated on the surface of Rhod-SP@MSN-CD to target integrin αvβ3 and αvβ5 overexpressed on cancer cells. Fluorescence imaging showed that both Rhod-SP@MSN-CD and Rhod-SP@MSN-CD-RGD were suitable for visualizing exogenous and endogenous Cu2+ in lysosomes of living cells. This strategy addresses some common challenges of chemical probes in biosensing, such as spatial resolution in cell imaging, the solubility and stability in biological system, and the interference from intracellular species. The newly designed nanoprobe, which allows one to track, on a location-specific basis, and visualize lysosomal Cu2+, offers a potentially rich opportunity to examine copper physiology in both healthy and diseased states.
- Li, Yinhui,Zhao, Yirong,Chan, Winghong,Wang, Yijun,You, Qihua,Liu, Changhui,Zheng, Jing,Li, Jishan,Yang, Sheng,Yang, Ronghua
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p. 584 - 591
(2015/02/19)
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- Ratiometric spiropyran-based fluorescent pH probe
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Spiropyran (SP) is an attractive molecular platform for the design of fluorescent OFF-ON probes for the detection of cations and anions operative on a ring-opening/closing mechanism. By incorporating a benzimidazole moiety at the ortho-position of the oxy
- You, Qi-Hua,Fan, Li,Chan, Wing-Hong,Lee, Albert W. M.,Shuang, Shaomin
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p. 15762 - 15768
(2013/09/12)
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- Ratiometric pH responsive fluorescent probes operative on ESIPT
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A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilita
- Chan, Yim-Pan,Fan, Li,You, Qihua,Chan, Wing-Hong,Lee, Albert W.M.,Shuang, Shaomin
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p. 5874 - 5879
(2013/07/27)
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- A novel calixsalen macrocycle: Metal sensing behavior for Zn2+ and intracellular imaging application
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The chiral [3+3] macrocycle 1 which displays a calixarene-like crystal structure has been synthesized. The UV/Vis and fluorescence spectral studies show that 1 and Zn2+ have a 1:3 complex stoichiometry. It exhibits high selectivity toward Znsu
- Zhu, Chengjian,Fu, Yong,Xing, Zhitao,Zhu, Chengcheng,Yang, Hongwei,He, Weijiang,Cheng, Yixiang
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supporting information; experimental part
p. 804 - 807
(2012/03/10)
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- Solid-state photochromism of 5-tert-butyl-2-hydroxyisophthalaldehyde
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Colorless crystals of 5-tert-butyl-2-hydroxyisophthalaldehyde change to an orange-red color upon brief exposure to UV-vis radiation (λ> 300 nm). The colored crystals revert to colorless in the dark. X-ray diffraction revealed different packing patterns for the crystals of nonphotochromic and photochromic compounds.
- Tanaka, Koichi,Watanabe, Yuta,Kalicki, Przemyslaw,Urbanczyk-Lipkowska, Zofia
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scheme or table
p. 727 - 729
(2012/08/08)
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- Synthesis and conformational aspects of 20- and 40-membered macrocyclic mono and dinuclear uranyl complexes incorporating salen and (R)-BINOL units
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20- and 40-membered macrocyclic mono and dinuclear uranyl complexes 11-13 incorporating salen and (R)-BINOL units have been designed and synthesized starting from 4-tert-butylphenol in eight steps. NMR measurements (COSY, NOESY/EXSY) indicate that such co
- Amato, Maria E.,Ballistreri, Francesco P.,Pappalardo, Andrea,Sciotto, Domenico,Tomaselli, Gaetano A.,Toscano, Rosa Maria
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p. 9751 - 9757
(2008/02/13)
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- An improved oxidation approach for preparing 4-substituted-2,6- diformylphenol by manganese(IV) dioxide
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The method for the oxidation of 4-alkyl-2,6-di(hydroxymethyl)phenol to 4-alkyl-2,6-diformylphenol (alkyl = Me or t-Bu) by activated manganese(IV) dioxide was improved, and also expanded to the oxidation of 4-chloro-2,6- di(hydroxymethyl)phenol. The resulting three dialdehydes were obtained in good yields.
- Huang, Wei,Gou, Shaohua,Hu, Dahua,Meng, Qingjing
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p. 1555 - 1561
(2007/10/03)
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- Mono- and diformylation of 4-substituted phenols: A new application of the duff reaction
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Careful control of the reaction conditions in a modified Duff reaction using anhydrous trifluoroacetic acid as the solvent enables the selective synthesis of either 4-substituted 2-formylphenols (5-substituted salicylaldehydes) or 4-substituted 2,6-diformylphenols in one step starting from commercially available 4-substituted phenols in moderate to good yield.
- Lindoy, Leonard F.,Meehan, George V.,Svenstrup, Niels
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p. 1029 - 1032
(2007/10/03)
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- Complexes with Macrocyclic Ligands, I. - Dinuclear Copper(II) Complexes with a Totally ?-Conjugated Macrocycle of Schiff Base Type: Syntheses, Structures, Electro-, and Magnetochemical Properties
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The dinuclear copper(II) complexes 6, 7, and 8 of three novel macrocyclic ligands were synthesized by the Schiff base condensation of 2 equiv. of 1,2-phenylenediamine and 2,6-diformylphenol in the presence of 2 equiv. of copper(II) perchlorate and were ch
- Brychcy, Klaus,Draeger, Klaus,Jens, Klaus-J.,Tilset, Mats,Behrens, Ulrich
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p. 465 - 476
(2007/10/02)
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- Valence Trapping in Mixed-Valence MnIIMnIII Complexes of a Macrocyclic Binucleating Ligand
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The electronic structures of two mixed-valence MnIIMnIII complexes, *H2O (2) and *0.5CH2Cl2 (3), and the MnII2 complex LMn2Cl2 (4) are probed.The L2- ligand is the dianion of the Schiff base
- Chang, Hsiu-Rong,Larsen, Scott K.,Boyd, Peter D. W.,Pierpont, Cortlandt G.,Hendrickson, David N.
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p. 4565 - 4576
(2007/10/02)
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- Synthesis, Characterization, and Chemical Reactivity of Soluble Bimetallomers
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The preparation, characterization, and redox chemistry of soluble Cu - Cu and Ni - Ni bimetallomers of 4-tert-butyl-2,6-bisformimdoyl>phenol with a variety of bridging ligands, Z, is described. The study of electroch
- Drago, Russell S.,Desmond, Michael J.,Corden, Barry B.,Miller, Karen A.
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p. 2287 - 2296
(2007/10/02)
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- Production of organic compounds
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Pyrogallol, and analogues thereof having an alkyl, carboxy or alkoxycarbonyl substituent in the benzene ring, and their salts, are prepared by oxidizing, preferably by hydrogen peroxide, the corresponding compounds in which 1 or 2 of the OH groups are replaced by --COR5 groups where R5 represents hydrogen, alkyl or phenylalkyl. The production of intermediates is also described and some of these are novel.
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