Thin film microfluidic synthesis of fluorescent highly substituted pyridines

Yasmin, Lyzu; Eggers, Paul K.; Skelton, Brian W.; Stubbs, Keith A.; Raston, Colin L.

doi:10.1039/c4gc00881b

Cited by 13 publications

(11 citation statements)

References 33 publications

(42 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The VFD has high shear stress in the dynamic thin films, and is effective for a wide range of applications, from organic synthesis to the fabrication of materials for both ‘top down’ and ‘bottom up’ approaches. For example, the VFD is effective in exfoliating single layered graphene and hexagonal boron nitride ( h ‐BN) sheets from the bulk material, wrapping of bacteria and algal cells with graphene and magnetic polymer, controlling the pore size and wall thickness of mesoporous silica, sol‐gel synthesis of silica xerogel at room temperature and the incorporation of curcumin, protein folding, accelerating enzymatic reaction, fabricating toroidal arrays of SWCNTs, laterally ‘slicing’ CNTs, probing the structure of self organized systems, biodiesel catalysis controlling chemical reactivity and selectivity and many others. The VFD is inexpensive relative to the SDP and RTP, and with novel operating characteristics, it is gaining prominence as a versatile microfluidic platform, albeit distinctly different to conventional microfluidics using channels where the fluid flow is usually laminar.…”

Section: Process Intensification: Continuous Flow Processingmentioning

confidence: 99%

Dynamic Thin Films in Controlling the Fabrication of Nanocarbon and Its Composites

Vimalanathan

Raston

2017

Adv Materials Technologies

Self Cite

View full text Add to dashboard Cite

journey of discovery for other carbon nano materials, which have properties beyond those of the classical allotropes of carbon. Other new forms of more recently established nanocarbon include single walled carbon nanohorns, [13,14] carbon nanoonions, [15][16][17] carbon nanorings, [18][19][20] cup-stacked carbon nanotubes [21,22] and carbon hybrid materials. [23] Methods for fabricating carbon nanomaterials have been extensively studied, in establishing robust syntheses, which is important for their use in down stream applications. Conventional methods of fabricating these materials have evolved, using both the 'top down' and 'bottom up' approaches, with some advance towards developing more benign processes and in addressing the often-vexing question of scalability of the methods, but this is often rather challenging. Centuries ago, elemental carbon was known to exist as two natural occurring allotropes, diamond and graphite, which have different structures and properties. Their physical and chemical properties depend on the arrangement of the carbon atoms. Diamond has a tetrahedral arrangement of sp 3 carbon atoms while graphite is comprised of stacked sheets of graphene held together by van der Waals interactions. Each graphene sheet consists of sp 2 carbon atoms arranged in two-dimensional hexagonal lattices. Diamond is typically used as a transparent electrical insulator while graphite is a black soft material with excellent electrical conductivity. The spark of a new era in allotropes of carbon beyond diamond and graphite began with the discovery of fullerene C 60 and other members of the fullerene family such as C 70 . [24,25] Of particular importance are the onedimensional (1D) carbon nanotubes and two dimensional (2D) graphene sheets, which have created new avenues in material science. The physical and chemical interactions of these carbon nanomaterials are determined mainly by their geometrical structure and method of synthesis. Conventional batch processing methods have dominated the field of fabricating carbon nanostructures in various morphologies and dimensions for specific applications, but they can have limitations, specifically in terms of environmental impact issues, economic sustainability, scalability and the quality of the material. The ability to precisely control the formation of a diverse range of functional materials at the nanoscale length, with scalability incorporated into the processing, is important for future uptake by industry in a myriad of applications. This review focuses on the use of continuous flow thin film microfluidic platforms for the Thin film microfluidics are developed for a wide range of applications, including the synthesis of various types of nanocarbon material, involving both 'top down' and 'bottom up' continuous flow processing. This type of processing addresses scalability at the inception of the science, and is applicable not just to the synthesis of nanocarbon, but also composites or hybrid material where one or more components is nanocarbon. This review introd...

show abstract

Section: Process Intensification: Continuous Flow Processingmentioning

confidence: 99%

Dynamic Thin Films in Controlling the Fabrication of Nanocarbon and Its Composites

Vimalanathan

Raston

2017

Adv Materials Technologies

Self Cite

View full text Add to dashboard Cite

show abstract

“…[11] The VFD is at hin film flow-chemistry platform that has emerged as effective technology in organic synthesis. [11][12][13][14][15][16] The VFD can operate under continuous flow,i nw hich reagents are introduced through jet feeds into the hemisphere of an inclined rapidlyr otatingt ube. The reagents experience high shear forces and intensem icromixing, with mechanoenergy delivered to the dynamic thin film in the rapidly rotatingg lass tube, dramatically accelerating organic reactions.…”

mentioning

confidence: 99%

Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine

Britton

Chalker

Raston

2015

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Thin film flow chemistry using a vortex fluidic device (VFD) is effective in the scalable acylation of amines under shear, with the yields of the amides dramatically enhanced relative to traditional batch techniques. The optimized monophasic flow conditions are effective in ≤80 seconds at room temperature, enabling access to structurally diverse amides, functionalized amino acids and substituted ureas on multigram scales. Amide synthesis under flow was also extended to a total synthesis of local anesthetic lidocaine, with sequential reactions carried out in two serially linked VFD units. The synthesis could also be executed in a single VFD, in which the tandem reactions involve reagent delivery at different positions along the rapidly rotating tube with in situ solvent replacement, as a molecular assembly line process. This further highlights the versatility of the VFD in organic synthesis, as does the finding of a remarkably efficient debenzylation of p-methoxybenzyl amines.

show abstract

“…[17] Processing in thin films can overcome these issues as demonstrated with the synthesis of 2,4,6-triarylpyridines (Figure 2B). [18],[10] Here, VFD-mediated conditions favored Michael addition over Schiff-base formation. This chemoselectivity contrasts the outcome in a round bottom flask, where uneven heating prevails and the opposite result occurs.…”

Section: Organic Transformationsmentioning

confidence: 99%

“…Amides, [21] biodiesel, [12, 16] esters, [7b] tri-alkylpyridines [10, 18] and photoredox products [11a] have benefited from VFD-based continuous flow. The high heat transfer present in the VFD has been used to improve the yields of acylation reactions using acyl chlorides.…”

Section: Organic Transformationsmentioning

confidence: 99%

Vortex Fluidic Chemical Transformations

Britton

Stubbs

Weiss

et al. 2017

Chemistry A European J

Self Cite

135

View full text Add to dashboard Cite

Driving chemical transformations in dynamic thin films represents a rapidly thriving and diversifying research area. Dynamic thin films provide a number of benefits including large surface areas, high shearing rates, rapid heat and mass transfer, micromixing, and fluidic pressure waves. Combinations of these effects provide an avant-garde style of conducting chemical reactions with surprising and unusual outcomes. The vortex fluidic device (VFD) has proved its capabilities in accelerating and increasing the efficiencies of numerous organic, materials and biochemical reactions. This MiniReview surveys transformations that have benefited from VFD-mediated processing, and identifies concepts driving the effectiveness of vortex-based dynamic thin films.

show abstract

Thin film microfluidic synthesis of fluorescent highly substituted pyridines

Abstract: Fluorescent polysubstituted pyridines are readily accessible as a single process using a thin film vortex fluidic device, with the compounds obtained in good yield following simple purification procedures.

Cited by 13 publications

References 33 publications

Dynamic Thin Films in Controlling the Fabrication of Nanocarbon and Its Composites

Dynamic Thin Films in Controlling the Fabrication of Nanocarbon and Its Composites

Rapid Vortex Fluidics: Continuous Flow Synthesis of Amides and Local Anesthetic Lidocaine

Vortex Fluidic Chemical Transformations

Contact Info

Product

Resources

About