22 research outputs found
Synthesis and Characterization of Naphthalenediimide-Functionalized Flavin Derivatives
Two acceptorāacceptor dyads have been synthesized featuring a flavin moiety and a naphthalenediimide (NDI) unit. The NDI unit is linked to the flavin through a short spacer group via either the N(3) or N(10) positions of the flavin. We have investigated the UV-Vis and redox properties of these multi-electron accepting systems which indicate that these materials display the collective properties of their component systems. Fluorescence spectroscopy measurements have revealed that their emission properties are dominated by the flavin unit
Correction: Zainalabdeen, N., et al., Synthesis and Characterization of Naphthalenediimide-Functionalized Flavin Derivatives. Int. J. Mol. Sci. 2013, 14, 7468ā7479.
Note: In lieu of an abstract, this is an excerpt from the first page. In the original version of the manuscript [1] some of the analytical data for compounds 1 and 2 were incorrect. The correct NMR data are presented below. The authors apologize for any inconvenience this may have caused to the readers of this journal. Compound 1: 1H NMR (500 MHz, DMSO-d6) Ī“ 11.64 (s, 1H), 8.73 (s, 4H), 8.57 (d, J = 1.4 Hz, 1H), 8.16 (dd, J = 8.9, 1.4 Hz, 1H), 7.81 (d, J = 8.5 Hz, 2H), 7.64 (d, J = 8.5 Hz, 2H), 6.99 (d, J = 8.9 Hz, 1H), 4.08 (t, J = 7.0 Hz, 2H), 3.28 (m, 2H), 1.69 (quin, J = 7.0 Hz, 2H), 1.33 (m, 8H), 0.86 (t, J = 6.8 Hz, 3H). 13C NMR (125 MHz, DMSO-d6) Ī“ 162.6 (2xC = 0), 162.3 (2xC = 0), 158.9, 155.1, 151.9, 140.8, 136.6, 136.1, 135.2, 133.7, 131.1 (2xC), 130.5 (4xC), 130.3 (q, J = 4 Hz), 128.6 (q, J = 4 Hz), 128.4 (2xC), 126.6, 126.5 (2xC), 126.4 (q, J = 31 Hz), 126.3 (2xC), 126.2, 123.2 (q, J = 271 Hz), 117.8, 39.9, 30.9, 28.5, 28.3, 27.1, 26.3, 21.9, 13.7. Compound 2: 1H NMR (500 MHz, CDCl3) Ī“ 8.77 (s, 4H), 8.58 (d, J = 1.4 Hz, 1H), 8.03 (dd, J = 9.1, 1.4 Hz, 1H), 7.87 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 9.1 Hz, 1H), 7.27 (d, J = 8.4 Hz, 2H), 5.37 (s, 2H), 4.61 (br s, 2H), 4.19 (t, 2H), 2.47 (sept, J = 6.7 Hz, 1H), 1.74 (m, 2H), 1.47ā1.23 (m, 10H), 1.07 (d, J = 6.7 Hz, 6H), 0.87 (t, J = 6.9 Hz, 3H). 13C NMR (125 MHz, CDCl3) Ī“ 163.1 (2xC = O), 162.9 (2xC = O), 159.0, 155.0, 149.9, 138.9, 137.5, 135.2, 134.9, 134.3, 131.7 (2xC), 131.5 (2xC), 131.2 (q, J = 4 Hz), 131.1 (4xC), 130.9 (q, J = 4 Hz), 128.6 (2xC), 127.1 (2xC), 127.0 (q, J = 28 Hz), 126.8 (2xC), 123.1 (q, J = 270 Hz), 116.9, 51.5, 44.9, 41.2, 31.9, 29.4, 29.3, 28.2, 27.6, 27.2, 22.8, 20.2 (2xC), 14.2
Structural phase transition and ferromagnetism in monodisperse 3 nm FePt particles
FePt nanoparticles with a size of 3 nm and thermally stable room-temperature ferromagnetism are investigated. The monodisperse nanoparticles were prepared by chemical synthesis and a salt-matrix annealing technique. Structural and magnetic characterizations confirmed the phase transition from the disordered face-centered cubic structure to the L10 structure with the chemical ordering parameter of 0.62Ā±0.05. Analysis in blocking temperature and fitting of temperature dependence of switching field reveals that the transformed 3 nm nanoparticles have a magnetic anisotropy constant of (2.8Ā±0.2) x 106 J/m3, smaller than those for the bigger particles and the fully ordered L10 bulk phase
Solvatochromic probes for detecting hydrogen-bond-donating solvents
Hydrogen bonding heavily influences conformations, rate of reactions, and chemical equilibria. The development of a method to monitor hydrogen bonding interactions independent of polarity is challenging as both are linked. We have developed two solvatochromic dyes that detect hydrogen-bond-donating solvents. The unique solvatochromism of the triazine architecture has allowed the development of probes that monitor hydrogen-bond-donating species including water
Recognition-Mediated Assembly of Quantum Dot Polymer Conjugates with Controlled Morphology
We have demonstrated a polymer mediated ābricks and mortarā method for the self-assembly of quantum dots (QDs). This strategy allows QDs to self-assemble into structured aggregates using complementary three-point hydrogen bonding. The resulting nanocomposites have distinct morphologies and inter-particle distances based on the ratio between QDs and polymer. Time resolved photoluminescence measurements showed that the optical properties of the QDs were retained after self-assembly
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Aromatic stacking interactions in flavin model systems
Flavins feature multiple attributes that explain their widespread occurrence in nature, including photostability, reversible electrochemistry, and especially the tunability of their optical, electronic, and redox properties by supramolecular interactions and modification of their chemical structure. Flavins are important redox cofactors for enzymatic catalysis and are central to a wide variety of processes, including biosynthesis, electron transport, photosynthesis, and DNA repair. The wide range of processes catalyzed by flavins makes them promising leads for synthetic catalysts. Their properties are also relevant to organic electronic and optoelectronic devices, where they have the potential to serve as photoactive electron carriers, a very uncommon property in current photovoltaic systems. In flavoenzymes, the flavin cofactor binds to the active site of the apoenzyme through noncovalent interactions. These interactions regulate cofactor recognition and tune the redox behavior of the flavin cofactor. In this Account, we describe the creation of host guest systems based on small molecule, polymer, and nanoparticle scaffolds that explore the role of aromatic stacking on the redox properties of the flavin and provide insight into flavoenzyme function. We also describe the creation of synthetic flavin-based interlocked structures featuring aromatic stacking interactions, along with the use of aromatic stacking to direct self-assembly of flavin-based materials. The interplay between redox events and aromatic stacking interactions seen in these synthetic models is important for fundamental understanding of biological systems including the flavoenzymes. The precise control of aromatic interactions and binding of flavins not only underpins their biological activity but gives them the potential to be developed into novel organic optoelectronic materials based on tuned synthetic flavin receptor assemblies. In a broader context, the redox properties of the flavin provide a very concise tool for looking at the role of electronics in aromatic stacking, an issue of general importance in biological and supramolecular chemistry.</p
Aromatic stacking interactions in flavin model systems
Flavins feature multiple attributes that explain their widespread occurrence in nature, including photostability, reversible electrochemistry, and especially the tunability of their optical, electronic, and redox properties by supramolecular interactions and modification of their chemical structure. Flavins are important redox cofactors for enzymatic catalysis and are central to a wide variety of processes, including biosynthesis, electron transport, photosynthesis, and DNA repair. The wide range of processes catalyzed by flavins makes them promising leads for synthetic catalysts. Their properties are also relevant to organic electronic and optoelectronic devices, where they have the potential to serve as photoactive electron carriers, a very uncommon property in current photovoltaic systems. In flavoenzymes, the flavin cofactor binds to the active site of the apoenzyme through noncovalent interactions. These interactions regulate cofactor recognition and tune the redox behavior of the flavin cofactor. In this Account, we describe the creation of host guest systems based on small molecule, polymer, and nanoparticle scaffolds that explore the role of aromatic stacking on the redox properties of the flavin and provide insight into flavoenzyme function. We also describe the creation of synthetic flavin-based interlocked structures featuring aromatic stacking interactions, along with the use of aromatic stacking to direct self-assembly of flavin-based materials. The interplay between redox events and aromatic stacking interactions seen in these synthetic models is important for fundamental understanding of biological systems including the flavoenzymes. The precise control of aromatic interactions and binding of flavins not only underpins their biological activity but gives them the potential to be developed into novel organic optoelectronic materials based on tuned synthetic flavin receptor assemblies. In a broader context, the redox properties of the flavin provide a very concise tool for looking at the role of electronics in aromatic stacking, an issue of general importance in biological and supramolecular chemistry.</p
One-Pot Green Synthesis of Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> 0D/2D Nanocomposites and Their Application in Noninvasive Point-of-Care Glucose Diagnostics
We
report a novel synthesis of Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> zero-dimensional (0D)/two-dimensional (2D) nanocomposites.
When bulk MoS<sub>2</sub> is exfoliated in the presence of thiol-functionalized
Fe<sub>3</sub>O<sub>4</sub> nanoparticles in water, the latter anchor
on the exfoliated MoS<sub>2</sub> nanosheets because of thiol affinity
toward MoS<sub>2</sub>, resulting in the Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> nanocomposites. The one-pot reaction, room temperature
processing, and use of aqueous solvents make the synthesis process
facile and ecofriendly. Because of the unique 0D/2D morphology, Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> nanocomposites show significantly
higher peroxidase-like catalytic activity compared to Fe<sub>3</sub>O<sub>4</sub> nanoparticles or MoS<sub>2</sub> nanosheets alone.
The enhanced catalytic activity has been used to detect glucose levels
down to 2.4 Ī¼M in absorbance measurements. Application toward
noninvasive point-of-care glucose diagnostics has been explored by
developing paper-based ādip and useā test strips that
show colorimetric response in the presence of glucose. To achieve
this, Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> nanocomposites along
with other active sensing elements are printed onto paper via a desktop
inkjet printer and cut into strips. When dipped into solutions of
various glucose concentrations, the test strips allow colorimetric
detection of glucose concentrations in a qualitative and quantitative
manner. To demonstrate practical usage, we have shown that the Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> nanocomposite-based glucose
test strips are sufficient to distinguish between normal (healthy)
and higher (diabetic) glucose concentrations with the naked eye. Because
of the simple and ecofriendly preparation and sensing efficacy with
low limit of detection, Fe<sub>3</sub>O<sub>4</sub>/MoS<sub>2</sub> nanocomposites show promise in noninvasive point-of-care medical
diagnostics