Probing the in-air growth of large area of 3D functional structures into a 2D supramolecular nanoporous network

Article abstract of DOI:10.1039/C8CC06125D

Surface-confined host-guest chemistry at the air/solid interface is used for trapping a functionalized 3D Zn-phthalocyanine complex into a 2D porous supramolecular template allowing the large area functionalization of an sp²-hybridized carbon-based substrate as evidenced by STM, resonance Raman spectroscopy, and water contact angle measurements.

Full text of DOI:10.1039/C8CC06125D

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LABET, C. Paris, C. Petit and A. Attias, Chem. Commun., 2018, DOI: 10.1039/C8CC06125D.
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Probing the in-air growth of large area of 3D functional structures
into a 2D supramolecular nanoporous network
Romain Brisse,a,b,c Dominique Guianvarc'h,b Christelle Mansuy,b Sandrine Sagan,b David Kreher,a
Lydia Sosa-Vargas,a Lydia Hamitouche,a Vincent Humblot,d Imad Arfaoui,c Vanessa Labet,c Céline
Paris,c Christophe Petitc and André-Jean Attiasa,e
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Abstract. Surface-confined host-guest chemistry at air/solid works focused only on 2D components, the interactions with
interface is used for trapping functionalized 3D Zn- the environment are limited to the upper surface. (ii) This is why
a
phthalocyanine complex into a 2D porous supramolecular template to go further in the functionalization, it is mandatory to develop
allowing the large area functionalization of a sp2-hybridized interactions in the dimension perpendicular to the surface.11 To
carbon-based substrate as evidenced by STM, resonance Raman address this issue, several approaches have been proposed,
spectrocopy, and water contact angle measurements.
based on covalent or noncovalent 3D structures able to project
into the third dimension and displaying a functionality.
Regarding the covalent 3D tectons, we can mention the
triazatriangulenium ions (TATA)-based platform12 and Janus
tectons platform13 developed for possible applications in the
fields of molecular machines and photonics, respectively. With
respect to noncovalent tectons, porphyrins (P) and
phthalocyanines (Pc) are interesting building blocks for
obtaining surface-confined self-assembly of 3D functional
tectons by metal complexation or axial ligation.14 Indeed, it has
been demonstrated that the macrocycle unit predominantly
adsorbs parallel to the substrate plane whereas the
coordination allows for the projection in the direction
perpendicular to the substrate plane. This has been reported for
multi-decker lanthanide porphyrin/phthalocyanine sandwich
complexes explored as molecular magnets and rotors on the
one hand,15 and zinc porphyrin (ZnP) derivatives coordinated
with a pyridine-based axial ligand (4-methoxypyridine, or 3-
nitropyridine) on the other hand.16 Among all the above
approaches, mounting on a metalated tetrapyrrole macrocycle
an appropriately functionalized axial ligand appears very
promising due to the versatile character and ease of the
coordination reaction. However, the macrocycles were
derivatized to steer the supramolecular self-assembly on the
substrate on the one hand, and the coordination occurred on
an already metallo-P covered surface on the other hand.
Supramolecular self-assembly of building blocks (tectons) at
surfaces has emerged as a powerful tool to pattern well-
organized monolayers on the nanoscale.1 The formation of the
two-dimensional (2D) supramolecular nanostructures is
achieved either under ultra-high vacuum (UHV) or at
liquid/solid interface.2 To go beyond the well-mastered
decorative 2D supramolecular self-assembly, the next challenge
is the realization by an easy process of large functional surfaces
in view of practical applications.3
Regarding the issue dealing with functionalization, two main
strategies have been developed: (i) the possibility to form 2D
surface‐confined supramolecular nanoporous networks and
takes advantage of their potential for hosting guests and
confined phenomena.4 Several functionalities have been
evidenced, ranging from the selective adsorption of guest
molecules,5
to
the
guest-induced
hierarchical
(multicomponent) nanostructures,6 control of the dynamic
properties of trapped species,7 site-selective immobilization of
guest molecules in periodically functionalized host cavities,8
photo-responsive host-guest systems,9 and cavity-confined
supramolecular coordination.10 However, since the above
a.IPCM, UMR CNRS-Sorbonne Université 8232, 4 Place Jussieu, 75005 Paris, France.
Email : andre-jean.attias@sorbonne-universite.fr
b.Sorbonne Université, École Normale Supérieure, PSL University, CNRS, Laboratoire
des biomolécules, LBM, 75005 Paris, France.
In previous works,17 we demonstrated that 1,3,5-
tristyrylbenzene derivatives substituted in positions 3 and 5 by
c. MONARIS, UMR CNRS-Sorbonne Université 8233, 4 Place Jussieu, 75005 Paris,
France. Email : christophe.petit@sorbonne-université.fr
alkoxy peripheral chains presenting n carbon atoms (TSB3,5-Cn
)
d.LRS, UMR CNRS-Sorbonne Université 7197, 4 Place Jussieu, 75005 Paris, France.
e. UMI Building Blocks for Future Electronics, CNRS - Sorbonne Université - Yonsei
University - Ewha Womans University, 50 Yonsei-ro Seodaemun-gu, Seoul, Korea.
(Scheme S1, ESI) are able to form, at liquid/solid interface, by
van der Waals interactions between alkyl chain on highly
oriented pyrolytic graphite (HOPG), surface-confined
nanoporous honeycomb networks able to act as 2D molecular
†
Electronic Supplementary Information (ESI) available: Synthetic details,
Experimental details, Raman spectroscopy, DFT modelling, and WCA images. See
DOI: 10.1039/x0xx00000x
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sieves. More particularly, it was shown that underivatized
phthalocyanine (Pc) could be immobilized in the TSB3,5-C12
cavities.18 Therefore, we propose to combine the cavity surface-
confined host-guest recognition and the metalloPc axial ligation
approaches to immobilize standing-up 3D functional guest
structures into the voids of a 2D host template.19 Moreover, we
provide a way for large area patterning and the associated
characterizations at different scales in air.
Here, we report the growth, by a drop-casting method at
air/HOPG interface, of large area (up to mm2) of 3D structures
from a 2D porous template and the multiscale characterization
by scanning tunneling microscopy (STM), Raman spectroscopy,
and contact angle measurements. With this aim, we first
synthesized a 3D functional tecton (ZnPc-L) consisting in a
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DOI: 10.1039/C8CC06125D
UV-Visible spectrum (sharp Q-band at 671 nm and absence of H
or J
Scheme 1 a) Complexation of ZnPc with L in chloroform and b) modeling of
the chemical structure of the complex by DFT calculations (see ESI).
shoulders).25 The progressive addition of aliquots of
L to the
ZnPc solution induced batho and hypochromic effects of the Zn-
Pc Q-band. In agreement with the literature,26 this was
attributed to the formation of the ZnPc-L complex. Saturation
was reached at about 150 eq. confirming the formation of ZnPc-
pyridine-based ligand (L) functionalized with a maleimide
function and mounted on a Zn-Phthalocyanine (ZnPc) (Scheme
1). The maleimide function was chosen to allow further thiol-
Michael addition click reaction widely used for biomolecular
synthesis and labelling of biomolecules.20 Our large area
patterning process consists in the following sequences: growth
of an ordered 2D porous network by drop-casting from a
TSB3,5-C12 solution in chloroform (CHCl3), solvent evaporation,
and subsequent drop-casting, on the dry host network film, of
a 3D ZnPc-L solution in CHCl3, to finally trap them in the
template pores. For comparison, similar experiments were
performed with planar ZnPc. After evaporation of the solvent,
STM images at air-HOPG interface only provide information of
the functionalized surfaces organization. Therefore, to get some
chemical information about the TSB3,5-C12 pores filling with
ZnPc or ZnPc-L molecules, the present work explores the use of
Raman spectroscopy and contact angle measurements. By
combining all the above techniques as well as DFT calculations,
we demonstrate that the 3D tectons build-up perpendicular to
the substrate projecting the maleimide function in a parallel
plane above the surface. Unexpectedly, the adlayer
hydrophilicity can be tuned depending on the guest molecules.
As axial ligand, we initially targeted the N-(4-
pyridyl)maleimide by reacting maleimide with 4-aminopyridine
(Scheme S2a, ESI).21 However, this attempt failed due to
propensity of maleic anhydride to polymerize in presence of
pyridine.22 Protecting the maleimide double bond, via the well-
known thermoreversible Diels-Alder (DA) reaction,23 gave also
unreproducible results and did not permit to prevent the
polymerization reaction (Scheme S2b, ESI), which could be
promoted by the high basicity of the pyridine ring in 4-
L
complex with a maximum rate.
In view of potential applications, it is necessary to prove the
functionalization at large scale. To address this issue, the use of
complementary techniques is needed. First, the supramolecular
self-assembly was investigated by STM. To circumvent the
complexification induced by working under UHV or at
liquid/solid interface, large-scale (200 x 200 nm2 up to 400 x 400
nm2) STM images were recorded at air/HOPG interface. With
this aim, are shown some representative STM images recorded
at different spots of the host nanoporous molecular monolayer
and the same sized images after addition of guest molecules,
i.e. ZnPc and ZnPc-L molecules (Fig. 1 and Fig. 2).
Figure 1a reveals that TSB3,5-C12 molecules form stable
long-range well-ordered 2D honeycomb structure at air-HOPG
interface. Then, it is possible to extract from Figure 1b unit cell
parameters associated to the 2D hexagonal packing (a = b = 4.2
nm and
 = 60.0°). Since they are similar within experimental
errors to those reported at phenyloctane-HOPG interface,17 the
drop-casting process does not affect the lattice parameters.
To demonstrate the trapping of ZnPc and its derivatives at
air/solid interface, first ZnPc molecules were deposited onto
the TSB3,5-C12 nanoporous monolayer (see ESI). Figure 2a
shows a typical STM image where almost the entire honeycomb
structure is filled by ZnPc molecules, appearing as bright spots.
These guest molecules are trapped by the host template and
they should lie flat on HOPG. It is also possible to observe some
features of the underlying nanoporous molecular monolayer.
Note that several areas of HOPG substrate having also smaller
ZnPc coverage rate are observed, probably due the wettability
and the fast drying of chloroform inducing local inhomogeneity.
Now, when the same experiment is performed with ZnPc-L
molecules, again the honeycomb structure is filled as shown on
Figure 2b. From the unit cell area of the nanoporous monolayer
(Figure 1b.), i.e. 15.3 nm2 (a = b = 4.2 nm), one deduces the
maximum coverage rate for ZnPc or ZnPc-L molecules onto the
nanoporous monolayer corresponds to 0.065 molecules per
nm2. Thus, the coverage rate is estimated to 92% ± 2% and 57%
± 2% for ZnPc (Figure 2a) and ZnPc-L (Figure 2b), respectively.
Although ZnPc-L molecules are expected to form a protrusion
aminopyridine (pKa = 9.2). This is why ligand
(Scheme S3, ESI), the synthetic route combining the use of the
less basic 4-aminomethylpyridine (pKa 4.3) with
L was targeted
=
protection/deprotection of the maleimide double bond via
DA/retro-DA reaction (see experimental details in ESI).
The coordination of ZnPc with ligand
L was operated in
solution and monitored by UV/Visible spectroscopy (FigS1, ESI).
Chloroform was chosen as solvent, owing to its poorly
coordinating capabilities and so as to maximize the
coordination rate of L with ZnPc.24 The obtained solution
contained monomeric ZnPc as evidenced by the shape of the
due to the presence of the ligand
corresponding to the black line AB (Fig. 2a and 2b, respectively)
L, cross-sections
2 | J. Name., 2012, 00, 1-3
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show that apparent height of ZnPc and ZnPc-L molecules are resonance Raman spectroscopy experiments for
a surface
similar, ~ 0.4 nm (Fig. S2, ESI). At this stage, one can only deduce concentration below the monolayer range. The main result of the
Figure 2. Nanoporous monolayer of TSB3,5-C12 molecules after addition,
by drop-casting, of guest molecules: a) ZnPc molecules, 200nm x 200nm
STM image, b) ZnPc-L complex molecules, 200nm x 200nm STM image.
All images have been recorded at air-HOPG interface in current mode
with -1.3V and 12pA as sample bias and tunneling current, respectively.
Figure 1. Well-defined nanoporous monolayer of TSB3,5-C12 molecules
deposited on HOPG by drop-casting. a) 200nm x 200nm long-range STM
image and b) 100nm x 100nm STM image of the supramolecular self-
assembly, recorded at air-HOPG interface in current mode with -1.3V
and 15pA as sample bias and tunneling current, respectively
resonance Raman investigations, lies in the observation of the ZnPc
signature. This means that its fluorescence is quenched by HOPG and
consequently confirms that the Pc macrocycles lie flat on HOPG.
As deduced from STM characterization and Raman
spectroscopy, it is not possible to assure the presence of the
that the nanoporous template is filled, but it is not possible to
distinguish between ZnPc and ZnPc-L molecules. Indeed, the
observed apparent height is due to electronic density at Fermi
level, although some authors claim that it should be possible to
distinguish between similar molecules through deep, long, and
tedious STM investigations whose results at few nanometer
scale are debatable.16
ligand
L on top of the ZnPc hosted inside the pores of the
TSB3,5-C12 supramolecular network. Since the deposition of
molecular species on a raw surface is known to change its
physical properties, we finally decided to track the presence of
In order to complement the information given by STM
measurements, another particular challenge for the fabrication
of sophisticated out-of-plane functional surfaces is the chemical
characterization of the different components used as building
blocks. With this aim, resonance Raman spectroscopy was used
to chemically probe the functionalization of the HOPG surfaces.
The 633 nm wavelength excitation was chosen, to be in the
absorption of the Q band (Fig. S1, ESI) of ZnPc and ZnPc-L. Figure S3
shows the spectra of TSB3,5-C12 deposited on HOPG, ZnPc and ZnPc-
L deposited inside TSB3,5-C12 network, as well as the spectra of pure
ZnPc and L molecules. At 633 nm, the Raman spectrum of TSB3,5-C12
deposited on HOPG exhibits only one band at 1582 cm-1, assigned to
the G-band of graphite (fig S3a). No peak from TSB3,5-C12 is detected
since we are outside the absorption range (~ 350 nm) of this
molecule. When ZnPc molecules are added into the TSB3,5-C12
templates, additional bands are clearly seen (Fig. S3b). The positions
of these bands are in agreement with those of the ZnPc powder (Fig.
S3d). Thanks to the resonance effect, we were able to detect the
presence of ZnPc on HOPG, in the pores of the TSB3,5-C12 network.
It is interesting to note that in the literature, even at 633 nm, the
Raman signal from Pc on HOPG is usually invisible.27 When ZnPc-L
molecules are added into the TSB3,5-C12 templates, the spectrum
(Fig. S3c) is similar to the one obtained after ZnPc addition. Thus, the
Raman signature of the ligand L is not observed, even the intense
bands at 1774, 1213, and 997 cm-1 (Fig. 3). Then, to understand this
result, simulated Raman spectra of ZnPc-L at 633 nm wavelength
excitation was computed (see ESI for calculation details, geometries
and spectra). The DFT calculations show that, if in the isolated L
ligand, the symmetric stretching of C=O bonds (흂̃~ퟏퟕퟖퟎ cm-1) is one
of the normal modes of the molecule with the highest Raman activity
below 3000 cm-1, it is no longer true in ZnPc-L. Indeed, in the
complex, the Raman activity of this normal mode appear about
several hundred times lower than that of the normal mode at
흂̃~ퟏퟓퟐퟎ cm-1 originating from the Pc moiety. Therefore, it is not
surprising that the C=O band could not be observed even by
ligand L by measuring the HOPG surface energy variations upon
modification by our surface-confined host-guest approach. This
is achieved by measuring the contact angle, Θ, a quantitative
measure of the wetting of a solid by a liquid.28 Moreover, this
macroscopic characterization is compatible with large area
substrates. Here, the water contact angles (WCA) of bare HOPG
and HOPG after deposition of TSB3,5-C12, ZnPc, and ZnPc-L
were determined (Fig. S3 and Table S1, ESI). The basal-plane
HOPG is known to be slightly hydrophilic,29 which is confirmed
by the value of Θ = 84.6° ± 0.8°. Depositing the non-polar
TSB3,5-C12 molecules should increases the hydrophobicity and
thus the WCA, as effectively observed (Θ = 91.2° ± 1.4°). On the
contrary, filing the pores of the TSB3,5-C12 network by
subsequent addition of ZnPc molecules, soluble in polar
solvents, should lead to a decrease of the WCA. This is
experimentally confirmed, the contact angle being equal to Θ =
85.7 ° ± 1.1°. Thus, angle contact measurement is sensitive
enough to estimate the change in HOPG surface state. Now, by
trapping the ZnPc-L complex instead of ZnPc in the 2D porous
Figure 3: Raman spectra (633nm) of HOPG surfaces with deposits of a)
TSB3,5-C12 b) TSB3,5-C12 and ZnPc and c) TSB3,5-C12 and ZnPc-L. d) and e) are
the Raman spectra of pure ZnPc and pure ligand L powders, respectively.
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Blunt, X. Lin, M. d. C. Gimenez-Lopez, M. Schroder, N. R.
template, a more significant change is observed as the WCA
strongly decreases from 91.2° ± 1.4° for the TSB3,5-C12 network
to 78.1 ° ± 1.3°. These results demonstrate the filling of the
pores by a species dissimilar to ZnPc and that modifies
drastically the hydrophilicity of the entire substrate. We can
infer that this molecule is the 3D ZnPc-L complex, its elbow
structure evidenced by modeling favoring the hydrophilicity.
Indeed, the two C=O bonds are available for H-bonding with
water molecules on the one hand, and, in addition, within this
geometry, ZnPc-L was computed to have a permanent dipolar
moment of 7.2 D on the other hand. Moreover, the
hydrophilicity tuning demonstrates the HOPG functionalization.
To summarize, we have developed a new method to trap
functional 3D ZnPc-L complex into a large 2D nanoporous
template. This facile process combines surface-confined host-
guest chemistry and drop-casting method. We describe an
unusual approach relying on the large-scale observation of the
functionalized surface allowing the use of several experimental
techniques as STM at air/solid interface, resonance Raman
spectroscopy, and contact angle measurements. By overlapping
the different results, it is possible to reliably prove the
controlled immobilization of the building block molecules at
long-range. Due to the versatility of the ligand complex
chemistry, our manipulable platform could be used for a new
generation of clickable surfaces for potential applications in e.g.
nanophotonics or biosensing.
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Conflicts of interest
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