Fluorescent Zn2+ chemosensors, functional in aqueous solution under environmentally relevant conditions

Lee, Amanda E.; Grace, Mike; Meyer, Adam G.; Tuck, Kellie L.

doi:10.1016/j.tetlet.2009.12.069

Cited by 28 publications

(12 citation statements)

References 27 publications

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“…Aer ltration, the pale yellow solid was puried by recrystallisation with NMP (N-methylpyrrolidone) and was dried under reduced pressure at 100 C to yield a yellow solid (2.68 g, 7.56 mmol, 72%), d H (300 MHz; DMSO-d 6 130.6 (triazine-C q -CH), 123.3 (triazine-C q ), 113.6 (NH 2 -C q -CH); FT-IR (ATR, 4000-400 cm À1 ) 3460, Synthesis of 9,10-anthracenedicarbaldehyde. 47 To a suspension of 9,10-dibromoanthracene (4.77 g, 13 mmol) in 200 mL of dry diethylether n-butyllithium (16,9 mL, 27 mmol) was added at À78 C. Aer stirring for 30 min at this temperature, the reaction mixture was allowed to warm up to room temperature. The solution was cooled down again to À78 C aer 1 h and DMF (4 mL, 52 mmol) was added dropwise.…”

Section: Methodsmentioning

confidence: 99%

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

et al. 2015

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Porous imine-linked networks (PINs) have been prepared by catalyst-free Schiff base condensation of 2,4,6-(4-aminophenyl)1,3,5-triazine with 9,10-anthracene-dicarboxaldehyde (PIN1 and PIN1_2) and with 4,4 0 ,4 00 ,4 000 -methanetetrakis-benzaldehyde (PIN2). Even after synthesis optimisation, only with DMSO (PIN1 and PIN2) microporous frameworks were obtained, whereas DMF (PIN1_2) and other solvents led to nonporous systems, estimated by argon measurements. Furthermore, 15 N solid state NMR and IR spectroscopy reveal the influence of the decomposition products of DMSO leading to protonation of the imine linkage and resulting in an ionic structure with an incorporated sulfonic counterion. Until now, protonation of an imine function due to the usage of DMSO as solvent has not been discussed in the literature. In contrast, for PIN1_2 the imine linkage remains neutral. Argon sorption isotherms for PIN1 and PIN2 exhibit surface areas of 458 m 2 g À1 and 325 m 2 g À1 and the pore structure displays micro-and small mesopores with pore diameters from 0.6 to 5 nm. Additionally, CO 2 isotherms at 273 K demonstrate ultramicropores for all three polymers with similar pore size distributions. Despite their different network structures, similar CO 2 uptakes (1.8-1.06 mmol g À1 at 273 K at 1.0 bar) and heat of adsorption Q st values of 30 kJ mol À1 were obtained. In line with the polyionic character of PIN1 and PIN2, both compounds adsorb three times more water than the more hydrophobic, neutral PIN1_2 at room temperature indicating two different adsorption mechanisms. IAST selectivity calculations show good CO 2 /N 2 (30-31) and CO 2 /CH 4 (8-12) selectivity factors. Despite their moderate BET-surface areas, the PINs show good CO 2 uptakes and selectivity factors.

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Section: Methodsmentioning

confidence: 99%

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

et al. 2015

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“…NMR spectra were recorded at 25 8C in CDCl 3 on a Bruker Avance 300 (300 MHz for 1 H and 75 MHz for 13 All commercially available products were used without further purification. The following dialdehydes were prepared according to literature: 9,10-diformylanthracene, [30] b,b'-p-phenylen-di-acrolein, [31] 2,6-naphthalenedicarbaldehyde, [32] 5-bromoisophthalaldehyde, [33] 4,4'-diformyl-1,1'-biphenyl, [34] 4,4'-diformylphenyl ether, [35] 2,5-diformylfuran, [36] 2,5-difor- Table 2. Electrochemical data [a] and HOMO energies [b] of complexes 1, 2 and 5. mylthiophene, [37] 5,5'-diformyl-2,2'bithiophene [38] and 1,1'-ferrocene dicarbaldehyde, [39] The following metal carbenes were prepared according to previously described methods:…”

Section: Methodsmentioning

confidence: 99%

“…All commercially available products were used without further purification. The following dialdehydes were prepared according to literature: 9,10‐diformylanthracene,30 b,b′‐ p ‐phenylen‐di‐acrolein,31 2,6‐naphthalenedicarbaldehyde,32 5‐bromoisophthalaldehyde,33 4,4′‐diformyl‐1,1′‐biphenyl,34 4,4′‐diformylphenyl ether,35 2,5‐diformylfuran,36 2,5‐diformylthiophene,37 5,5′‐diformyl‐2,2′bithiophene38 and 1,1′‐ferrocene dicarbaldehyde,39 The following metal carbenes were prepared according to previously described methods: pentacarbonyl[(ethoxy)(methyl)carbene]chromium(0) ( 3 a ),40 pentacarbonyl[(ethoxy)(methyl)carbene]tungsten(0) ( 3 b ),41 decacarbonyl‐μ‐[1,4‐phenylenbis(1‐ethoxy‐2‐propen‐3‐yl‐1‐yliden)]dichromium ( 2 aa )13 and decacarbonyl‐μ‐[1,3‐phenylenbis(1‐ethoxy‐2‐propen‐3‐yl‐1‐yliden)]dichromium ( 2 ab ) 13…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structure, and Electronic Properties of Extended π‐Conjugated Group 6 Fischer Alkoxy–Bis(carbene) Complexes

Chu

Fernández

Sierra

2013

Chemistry A European J

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The synthesis, structure and electronic properties of novel Group 6 Fischer alkoxy-bis(carbene) complexes are reported. The UV/Vis spectra of these species display two main absorptions at approximately 350 and 550 nm attributable to a ligand-field (LF) and metal-to-ligand charge-transfer (MLCT) transitions, respectively. The planarity of the system and the cooperative effect of both pentacarbonyl metal moieties greatly enhance the conjugation between the group at the end of the spacer and the metal carbene fragment provoking dramatic changes in the LF and MLCT absorptions. This is in contrast to related push-pull Fischer monocarbenes, where the position of the MLCT band remains mostly unaltered regardless the substituent attached to the donor fragment. In addition, the MLCT maxima can be tuned with subtle modifications of the electronic nature of the central aryl fragment in the novel A-π-D-π-A (A = acceptor, D = donor) systems. DFT and time-dependent (TD) DFT quantum chemical calculations at the B3LYP/def2-SVP level have also been performed to determine the minimum-energy molecular structure of this family of compounds and to analyse the nature of the vertical one-electron excitations associated to the observed UV/Vis absorptions as well as to rationalise their electrochemical behaviour. The ability of tuning up the electronic properties of the compounds studied herein may be of future use in material chemistry.

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“…9,10‐Dibromoanthracene ( 1 ) was purchased from Sigma Aldrich. The synthesis of 2 , 3 , 4 , 5 , 7 , 8 , 9 , and P1 was performed according to the descriptions in literature.…”

Section: Methodsmentioning

confidence: 99%

Polymers with alternating anthracene and phenylene building blocks linked by ethynylene and/or vinylene units: Studying structure‐properties‐relationships

Boudiba

Růžička

Ulbricht

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Four conjugated polymers (P1-P4) consisting of alternating anthracene-9,10-diyl and 1,4-phenylene building blocks connected via ethynylene as well as vinylene (P1 and P2), ethynylene-only (P3), and vinylene-only (P4) moieties, respectively, were synthesized and studied. The phenylene units in all four polymers bear 2-ethylhexyloxy side-chains to promote good solubility. The three polymers with vinylene units (P1, P2, and P4) were prepared using the Horner-Wadsworth-Emmons reaction. For the synthesis of the aryleneethynylene polymer P3, the palladium-catalyzed Sonogashira cross-coupling reaction was used. The polymers were characterized by NMR, Fourier transform infrared spectroscopy, and Raman spectroscopy. Photophysical, absorption and photoluminescence, and electrochemical properties were studied. Spectroscopic ellipsometry measurements were performed to gain more insight on the optical properties. In addition, the transport properties were investigated using admittance spectroscopy. The bulk hole mobility and its dependence on the electric field were evaluated for P1 and P2.

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Fluorescent Zn2+ chemosensors, functional in aqueous solution under environmentally relevant conditions

Cited by 28 publications

References 27 publications

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Porous imine-based networks with protonated imine linkages for carbon dioxide separation from mixtures with nitrogen and methane

Synthesis, Structure, and Electronic Properties of Extended π‐Conjugated Group 6 Fischer Alkoxy–Bis(carbene) Complexes

Polymers with alternating anthracene and phenylene building blocks linked by ethynylene and/or vinylene units: Studying structure‐properties‐relationships

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