Insights into the photophysics,protonation and Cu2+ ion coordination behaviour of anthracene-9,10-dione-based chemosensors

Carboxylic acid–diamine-based Cu²⁺ chromogenic sensors (3 and 4) exhibited colour switching from red to blue with good sensitivity and selectivity towards Cu²⁺ among other physiologically important alkali, alkaline earth and heavy metal ions. This colour-switching phenomenon arises due to selective deprotonation of aryl amine NH by Cu²⁺. Significantly, chemosensor 3 (λ_max 492 nm) shows multiple modes of complexation towards Cu²⁺. It is very much evident from the appearance of blue colour (λ_max 615 nm) at pH >7.0 and yellow colour (λ_max 465 nm) at pH < 4.0. In addition, chemosensor 3 exhibits a unique logic gate system that involves ‘INHIBIT’ and ‘TRANSFER’ logic gates.     

Synthesis and in vitro antitumor activity of substituted anthracene-1,4-diones

Based on a rational approach, 6-substituted 1,4-anthracenediones were synthesized and found to exhibit potent cytotoxic activity against murine and human leukemic cells. The synthetic sequence includes a double Friedel-Crafts reaction, reductive quinone formation, and selective bromination of the alkyl side chain. A key intermediate, 6-bromomethyl-1,4-anthracenedione (10), was synthesized and converted to various active antitumor agents, including a water-soluble phosphate ester pro-drug. The interconversion reactions include displacement of the bromide with various nucleophiles and basic hydrolysis to the alcohol and subsequent oxidation to provide the aldehyde. Based on their ability to decrease L1210 and HL-60 tumor cell viability, 1,4-dihydroxyanthraquinones are inactive but 1,4-anthracenediones have interesting antitumor activity, which may be abolished by modification of the A-ring and improved by substitution of the C-ring. The cytostatic and cytotoxic activity of the representative compound 10 was verified at the National Cancer Institute in studies on the 60-human tumor cell line panel in the in vitro antitumor screening. A wide spectrum of tumor cells are sensitive to 10 inhibition, and concentrations required to inhibit tumor cell growth by 50% (GI₅₀) at 48 h are <10 nM in HL-60 and MOLT-4 and 37.1 nM in SR leukemia. Preliminary studies suggest that the molecular targets and mechanisms of action of 10 may be different from those of daunomycin.     

Surface-Enhanced Infrared Spectral Investigations of 2,3-Bis(chloromethyl)anthracene-1,4,9,10-tetraone on Copper Nanoparticles

ABSTRACT

Surface-enhanced infrared (IR) absorption spectroscopic technique has been employed to investigate the orientation of 2,3-bis(chloromethyl)anthracene-1,4,9,10-tetraone (BCMAT) on copper nanoparticles (NPs). Copper NPs have been prepared by the chemical reduction method. The observed ring stretching modes show higher downshifts, broader bandwidths, and higher enhancement. The observed features in out-of-plane and in-plane CH deformation modes indicate that the BCMAT molecules may be adsorbed in a “flat-on” orientation on the copper NPs. The observed lower enhancement factor of the in-plane C?O deformation mode and C?O stretching mode and the higher enhancement factor of out-of-plane C?O deformation mode elucidate that the BCMAT molecules are adsorbed on the copper NPs in a “flat-on” orientation. All these observations show that BCMAT is adsorbed on copper NPs through the π-anthraquinone ring system in a “flat-on” orientation.     

Synthesis and Characterization of New Self-Colored Blue Waterborne Polyurethane Based on a Colorant Diol as Chain Extender

A series of novel self-colored blue waterborne polyurethanes (BPUs) were successfully synthesized by incorporating a self-made colored diol 1,4-bis(2-hydroethylamino)anthrancene-9,10-dione (BHAD) into the polyurethane backbone via step growth polymerization. FTIR, ¹H NMR, ultraviolet-visible (UV-vis) spectroscopy were used to characterize BHAD and BPUs. Compared with BHAD, BPUs showed hypochromic change in UV-visible spectroscopy. The obtained BPUs have good thermal dye migration. The effect of BHAD content on BPUs’ emulsion stability, water resistance, mechanical properties, and thermal performance were investigated systematically by particle size analysis, water absorption ratio, tensile strength test, and thermogravimetric analysis.     

A Two-dimensional Anthracene-9,10-dicarboxylate Zinc(Ⅱ) Coordination Polymer Based on Binuclear [Zn_2Cl_2] Nodes: Synthesis,Characterization and Luminescent Properties

A two-dimensional(2D) 44 topological ZnⅡ coordination polymer {[Zn2Cl2(L)(4bpy)2]}∞(H2L = anthracene-9,10-dicarboxylic acid, 4bpy = 4,4ˊ-bipyridine) based on binuclear [Zn2Cl2] nodes has been synthesized and characterized by IR, elemental analysis, X-ray powder diffraction and single-crystal X-ray diffraction analysis. Moreover, the luminescent properties of the correspon- ding compound have been briefly investigated.     

Liquid chromatography coupled to on-line post column derivatization for the determination of organic compounds: A review on instrumentation and chemistries

Analytical derivatization either in pre or post column modes is one of the most widely used sample pretreatment techniques coupled to liquid chromatography. In the present review article we selected to discuss the post column derivatization mode for the analysis of organic compounds. The first part of the review focuses to the instrumentation of post-column setups including not only fundamental components such as pumps and reactors but also less common parts such as static mixers and back-pressure regulators; the second part of the article discusses the most popular “chemistries” that are involved in post column applications, including reagent-less approaches and new sensing platforms such as the popular gold nanoparticles. Some representative recent applications are also presented as tables.     

Synthesis of new functionally substituted fullerenopyrrolidines

New fullerenopyrrolidines were synthesized by the three-component reactions of fullerene C₆₀, N-methylglycine, and aromatic aldehydes, viz., N,N-bis(2-chloroethyl)-4-aminobenzaldehyde, N-(2-chloroethyl)-N-methyl-4-aminobenzaldehyde, indole-3-carbaldehyde, 4-phenylbenzaldehyde, and anthracene-9-carbaldehyde. The structures of the resulting compounds were established by spectroscopic methods.     

A Novel Palladium（II） Complex Self-assembled from Anthracene-9-carboxylic Acid： Synthesis, Crystal Structure and Spectroscopic Properties

A novel palladium（II） complex [（TMEDA）Pd（anca）2].2DMSO （1, TMEDA = N,N,N＇,N＇-tetramethylethylethylenediamine, anca = anthracene-9-carboxylic acid） was synthesized and characterized by single-crystal X-ray diffraction, 1H NMR, UV-Vis and fluorescence spectroscopy. The cell belongs to orthorhombic Aba2 space group with a = 19.698（7）, b = 21.045（7） c = 9.062（3） A, Z = 4, V= 3757（2） A3, C40H46N206PdS2, Mr = 821.31, D, = 1.452 g/cm3, F（000） = 1704, the final R = 0.0272, wR = 0.0667 and GOOF = 0.999. Complex 1 exhibits an interesting distorted clip-shaped molecular configuration which is stabilized by intramolecular C-H...O hydrogen bonds. The cells are packed into a 3D supramolecular structure based on the intermolecular C-H...zr interactions which further construct the tubular channels serving as guest molecular channels to include the DMSO solvent molecules inside. Furthermore, the spectroscopic properties of 1 were also investigated.