3D Micropatterned All-Flexible Microfluidic Platform for Microwave-Assisted Flow Organic Synthesis

Article abstract of DOI:10.1002/cplu.201700440

A large-area, all-flexible, microwaveable polydimethoxysilane microfluidic reactor was fabricated by using a 3D printing system. The sacrificial microchannels were printed on polydimethoxysilane substrates by a direct ink writing method using water-soluble Pluronic F-127 ink and then encapsulated between polydimethoxysilane layers. The structure of micron-sized channels was analyzed by optical and electron microscopy techniques. The fabricated flexible microfluidic reactors were utilized for the acetylation of different amines under microwave irradiation to obtain acetamides in shorter reaction times and good yields by flow organic synthesis.

Full text of DOI:10.1002/cplu.201700440

Accepted Article
Title: 3D Micropatterned all Flexible Microfluidic Platform for Microwave
Assisted Flow Organic Synthesis (MAFOS)
Authors: Deniz Hur, Mehmet Girayhan Say, Sibel Emir Diltemiz, Fatma
Duman, Arzu Ersöz, and Rıdvan Say
This manuscript has been accepted after peer review and appears as an
Accepted Article online prior to editing, proofing, and formal publication
of the final Version of Record (VoR). This work is currently citable by
using the Digital Object Identifier (DOI) given below. The VoR will be
published online in Early View as soon as possible and may be different
to this Accepted Article as a result of editing. Readers should obtain
the VoR from the journal website shown below when it is published
to ensure accuracy of information. The authors are responsible for the
content of this Accepted Article.
To be cited as: ChemPlusChem 10.1002/cplu.201700440
Link to VoR: http://dx.doi.org/10.1002/cplu.201700440
A Journal of
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ChemPlusChem
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3D Micropatterned all Flexible Microfluidic Platform for
Microwave Assisted Flow Organic Synthesis (MAFOS)
Deniz Hür,*,a,b Mehmet G. Say,b,c Sibel E. Diltemiz,a,b Fatma Duman, Arzu Ersöz, Rıdvan Saya,b
a
a,b
Dedication ((optional))
Abstract: In present work, we have fabricated large area, all flexible
and microwaveable PDMS microfluidic reactor that has printed via 3D
bioplotter system. The sacrificial microchannels have printed on
Polydimethoxylane (PDMS) substrates by direct ink writing method
using water soluble Pluronic F-127 ink and encapsulated between
PDMS layers. The structure of micrometer sized channels has
analyzed by optical and electron microscopy techniques. The
fabricated flexible microfluidic reactors have utilized for acetylation of
different amines under microwave irradiation to get acetylamides in
shorter reaction time and good yields in Microwave Assisted Flow
Organic Synthesis (MAFOS).
Different 3D printing methods have been applied in literature.
These are: a) Inkjet 3D printing in which both drop on
demand and continuous printing modes are applicable [25], b)
Stereo lithography, where objects are printed layer-by-layer
using photo polymerization of monomers [26], c) Two-photon
polymerization method, where near-infrared femtosecond
laser is applied on material for polymerization [27, 28]
.
3D printing has been used to use in the area of microfluidics
[29, 30],
in order to fabricate microfluidic networks and chips
2
9
[31-34]
utilizing microvascular networks , tissue engineering
and chemical synthesis applications [35]. On the other hand
D printed mesoreactors are available in literature [36]. These
Introduction
3
Based on their excellent mass and heat transfer rates, short
reaction times and selective reaction ability; microfluidic
systems which are fabricated using several materials (i.e.
glass, polypropylene (PP), polydimethoxysilane (PDMS),
Teflon (PTFE), steel etc.) in different shapes, have large
applications can be realized by using different types of 3D
printing technologies such as STL based printing [37], Fused
Deposition Modelling [33] and direct-ink writing of sacrificial
inks [38, 39]. Details of these techniques and applications have
been published as a review by Au and co-workers [40]
.
[
1-6]
application area in synthesis of organic
and
3D printing/writing of sacrificial hydrogels and fugitive
inks are one of the escalating technologies to create
microfluidic channels. Liquid metals [41], bio-polymer based
hydrogels [42, 43] and Pluronic based [32, 44] inks have been
used to fabricate sacrificial patterned micro networks. Among
these techniques, Pluronic F-127 based inks are chosen for
superior properties such as easy to print, room temperature
writing of the inks and controlled ink rheology. In addition,
printed networks with this material can be removed easily
after encapsulation because of thermally reversible gelation
properties of the Pluronic F-127 [45]. These properties make
Pluronic F-127 inks excellent candidate for creating fugitive
networks for microfluidic application.
[
7-9]
pharmaceutical
products as well as inorganic
nanoparticles [10-17]. Micron scaled electromagnets have
prepared in PDMS microfluidic [18]. Additionally, continuous
microfluidic reactors have developed for polymer particles
[19].
Several bio application methods of microfluidics have
been reviewed in 2011[20]. Enzymatic catalysis works have
been conducted using flow reactors [21]. Among different
fabrication methods, three dimensional (3D) printing of
microfluidic systems have great application area [22-24].
[
a]
Deniz Hür,* Sibel E. Diltemiz, Fatma Duman, Arzu Ersöz, Rıdvan
Say
Science Faculty, Chemistry Department
Anadolu University, Yunus Emre Campus 26470, Eskişehir, Turkey
PDMS is one of the superior material for production of
microfluidic devices based on its transparency, non-toxicity,
flexibility, chemical inertness, and non-flammable properties.
This widely used material in microfluidics field is generally
bonded to a glass slide or sandwiched between another
PDMS layer by oxygen plasma. Additionally, three aspects
of compatibility (swelling, dissolution of PDMS oligomers in a
solvent and solute dispersion between solvent and PDMS)
E-mail: dhur@anadolu.edu.tr
[
b]
c]
Deniz Hür,* Sibel E. Diltemiz, Arzu Ersöz, Rıdvan Say
Bionkit Co.Ltd. Anadolu University Teknopark, 26470 Eskisehir,
Turkey.
[
Mehmet G. Say
Current Address: Laboratory of Organic Electronics, Department of
Science and Technology, Linköping University, 60174 Norrköping,
Sweden
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))
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for PDMS were investigated and shown that PDMS can be
useful fabrication material for microfluidics area [46].
Previously PDMS was used for fabrication of microfluidic
devices with different fabrication techniques and various
applications in literature [47-50]
.
Presented work here, describes and introduces a novel 3D
micro patterning method for creating microfluidic reactors using
Pluronic F-127 ink by direct ink-writing technique and PDMS
encapsulation. We demonstrated fabrication procedure of all-
flexible, transparent, low cost microfluidic reactor, which is
completely compatible for microwave flow synthesis conditions. In
particular, high reusability of these devices allows us to run
experiments in MAFOS without losing efficiencies. MAFOS has
been employed in research laboratories and industry based on
their safe process at elevated temperatures and pressures, and
also acceleration effect of microwave (MW) on reactions[51-55]
.
Results and Discussion
3D Fabrication of all Flexible Microfluidic
In the present work, 3D micro patterns we plotted using water
soluble Pluronic F-127 ink and encapsulated this printed
structures in PDMS matrix to fabricate microwaveable, all flexible,
low cost PDMS based microfluidic reactors. Aqueous solution of
highly concentrated co-polymer, wax like Pluronic F127, which
consists Poly(propylene oxide) (PPO) center with Poly(ethylene
oxide) (PEO) side chains, was used as sacrificial ink. Fabrication
of 3D printed microfluidic reactors consisted of several steps
(
Figure 1). The fabrication started with preparation of flexible
substrate. 15-20 mL of PDMS mixture was poured into 12 cm petri
dishes and cured at 70 ⁰C for 5 h. The Pluronic F-127 (40 w/v %)
sacrificial ink was printed using 3D-Bioplotter (EnvisionTEC,
Germany) onto substrate with optimized bio printing parameters
Figure 1. 3D microfabrication method of all flexible PDMS micro reactor. a)
Plotting cold, gel Pluronic F-127 on PDMS in petri dish. b) Covering and curing
printed micro channels with second layer of PDMS. c) Removal of Pluronic F-
(
Table 1, see movie S1). Next, 3D bio printed pattern was
encapsulated with PDMS (15-20 ml) and cured at room
temperature overnight (see sup. Fig. 4). Finally, withdrawal of the
Pluronic F-127 was performed by constantly circulation of cold
water and ethanol throught the channel in minutes. The removal
of the ink was controlled with UV-Vis spectra at 220 nm after
washing microfluidic with 10, 20, 30 mL water in flow rate of 2
mLmin-1 [56] Subsequently, micro reactors were connected with
standard PTFE tubing by plugging PTFE tubing and insulation
with household construction silicon.
1
27 ink by pumping cold water in micro channel. Inset shows SEM image of
PDMS channel (scale bar 400 µm)
Detailed Optical microscope and SEM images were recorded for
Pluronic F-127 microchannel to analyze dimensions of printed
structure dimensions (Figure 2). Printed networks were fabricated
by using 250 µm plastic needle tips. As depicted in figure 2, direct
ink written layers demonstrated perfect shape and precise
dimensions. Thus, smooth lines of Pluronic F-127 inks can be
printed having channel widths vary from 300 µm to 570 µm (figure
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S5). The total lenght of channel is 58.4 cm and volume is 0.35
mL.
with organic solvent due to after swelling and peeling of PDMS
cause leakage of liquid. In another fabrication method, a
microfiber was embedded in PDMS, after curing, microfiber was
pulled away for tunneling microchannel in PDMS block[57]. This
method has disadvantage due to pulling away procedure needs
straight microfiber. Thus, channels has to be line shaped.
Table 1. Printing parameters for 40 w/v % Pluronic F-127 ink to fabricate
microfluidic networks.
Pluronic F-127 Sacrificial Ink
Needle Diameter (mm)
Printing Temperature (⁰C)
Printing (XY) Speed (mm/s)
Pressure (bar)
0.25
Presented fabrication method, in this research, deals with
preventing of these disadvantages of previous methods by
introducing all flexible and unlimited shaped microchannel in
PDMS microfluidic devices. Although, swelling of PDMS in
organic solvents has been judged as a disadvantage before, since
our 3D plotted microfluidics fabricated from only PDMS, swelling
will not be caused to leakage and deformation. According to figure
14 ⁰C – 22 ⁰C
8 – 10
0.4 – 0.9
- 0.1 – 0.1
~ 100
Postflow & Preflow delay (s)
Amount of Ink Used (µl)
Printing time (s)
40
Dimensions (mm)
65 x 17 x 0.3
3, small change was observed on structure of microchannel after
five reactions (swelling and deswelling). Detailed SEM
investigations showed that width of microchannel is 571.0 µm and
5
90.8 µm before reaction and after reactions, respectively. In the
image of cross section of hollow microchannel as shown in Figure
c, the width of semi-circular structure is between 400 µm - 1 mm
3
that can be changed by applying different 3D printing parameters.
Supporting Figure S5 and Figure S6 provide additional optical and
SEM images for further analysis of printed and encapsulated
layers.
Figure 2. (a) Optical microscope image of Pluronic F-127 networks (b) SEM
image of printed line.
All previous literature for fabrication of micro reactor and
microfluidics via PDMS were based on lithographic method where
microchannel was produced by photoresist SU-8 shaped PDMS
mold. Afterward this lithographed PDMS was stacked on glass
using plasma to prepare half-flexible PDMS-glass integrated
microfluidic. Since adhesion between glass and PDMS has
limitations this microfluidics cannot be used in heated systems
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N-acetylbenzotriazole, 1, and several amines, 2, under 100 W
microwave irradiation in tetrahydrofuran (THF) at 0.3 mLmin-1 flow
rate at 67 ºC was given 3a-e in 92-96 % yields, to prove the
usability of fabricated microfluidic reactor in microwave system
with organic solvents.
Structure of products were characterized by 1H and 13C NMR.
(
see Supp.Info.)
Figure 4. Schematic representation of MAFOS procedure, synthesis procedure
of Acetylamides 3a-e.
By using fabricated microfluidic reactor under microwave
irradiation, positive effects of both flow and microwave on organic
reactions were applied. Reaction yield and times were
comparable with both conventional and microwave reflux
methods (Table 2).
Figure 3. SEM images of microfluidic device (a) before reaction (b) after
reaction (swelling and deswelling) (c) cross-section view of PDMS microchannel.
Scale bars show 200 µm.
Table 2. Structure, yields and reaction times of products 3a-e.
Isolated yield (%) /
R
Acetylamide 3a-e
reaction time
min)
(
Usage of Fabricated Microfluidic in Microwave Organic
Synthesis
94 / a
3a
To demonstrate effectiveness of flexible micro-reactors in
MAFOS applications, PTFE tubings were plugged into inlets and
outlet of microfluidic device, then the micro-reactor was used for
the organic synthesis of acetylamides. In microwave setup, micro-
reactor was placed in microwave chamber and reagents were
pumped in with a peristaltic pump (Figure 4). Reaction between
92
3b
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We believe that combining with microwave transparent solvents,
transparency of PDMS will be great opportunity for MAFOS. In
future works, we plan to modify PDMS surface with organic
catalysis bearing trimethoxysilyl (-Si(OMe)3) moiety to coat
9
6
3c
9
4 / a
4/ a
microfluidic’s walls with different heterogeneous catalysts[58]
.
3d
9
3e
Experimental Section
a) overall microwave flow reaction 15 min., residual time 1.16 min., reflux under
microwave in 30 min. resulted in 90% yield, conventional heating in 5 hours
resulted in 73% yield.
General Synthesis of N-acetylamides in PDMS Microfluidic
under Microwave Irradiation
THF (15 mL) dissolved N-acetylbenzotriazole (3 mmol) and
amines (3 mmol) were pumped in PDMS microfluidic reactor with
Since PDMS is microwave transparent, reaction temperature is
easily followed using IR sensor which has minimum surface area
of 8-14 µm implemented in CEM Discover Microwave Reactor.
Only one microfluidic device was used for all reactions and no
deformation was observed. Thus, it can be concluded that PDMS
micro-reactor has high usability in these reaction conditions.
.3 mLmin-1 flow rate in CEM Discover microwave instrument.
0
Continuous 100 W MW was applied with continuous air cooling
during the reaction. The overall reaction time was 15 min and
residual reaction time was calculated as 1.16 min (volume of
-1
microfluidic / flow rate = 0.35 mL / 0.3 mLmin = 1.16 min) After
finishing reaction, solvent was removed under vacuum. Crude
product was dissolved in ethyl acetate and extracted with 20 %
Conclusions
aqueous Na
2 3
CO solution to remove 1H-benzotriazole. Organic
Several additive manufacturing techniques have been used to
fabricate submillimeter and millimeter fluidics. However, our
technique allows that user defined, computer aided design micro-
pattern generation, which paves the way of large area, flexible
and stretchable microfluidics applications.
layer was dried over Na
2
SO
4
to give N-acetylamides in 92-96 %
1
isolated yield. Structure of products were characterized using H
and 13C NMR analyses (see supp. info.).
Keywords: all flexible microfluidic • microwaveable microfluidic •
In this work, we introduced a novel 3D fabrication method of all
flexible (Figure 5), PDMS microfluidic reactor. This microfluidic
device successfully used in microwave flow organic synthesis for
acetylation of several amines.
3D printed PDMS microfluidic • flow synthesis • acetylation
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3
D Fabricated all flexible PDMS
,
Deniz Hür,* Mehmet G. Say, Sibel E.
Diltemiz, Fatma Duman, Arzu Ersöz,
Rıdvan Say
microfluidic was used for the
Microwave Assisted Flow Organic
Synthesis (MAFOS) of acetylation of
several amines.
Page No. – Page No.
3D Micropatterned all Flexible
Microfluidic Platform for Microwave
Assisted Flow Organic Synthesis
(
MAFOS
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