Artificial light-harvesting supramolecular polymeric nanoparticles formed by pillar[5]arene-based host-guest interaction

Article abstract of DOI:10.1039/c7cc09315b

Artificial light-harvesting nanoparticles were prepared from supramolecular polymers comprised of pillar[5]arene with anthracene-derived donors and acceptors through host-guest interactions. The resulting water-dispersible nanoparticles displayed efficient energy transfer and excellent light harvesting ability in part because the steric bulk of pillar[5]arene suppressed the self-quenching of the chromophores.

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Artificial Light-harvesting Supramolecular Polymeric Nanoparticles
Formed by Pillar[5]arene-based Host–guest Interaction
Cai-Li Sun,ab Hui-Qing Peng,b Li-Ya Niu,a Yu-Zhe Chen,b Li-Zhu Wu,b Chen-Ho Tung,b and Qing-Zheng
Yang*a
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Artificial light-harvesting nanoparticles were prepared from
A promising strategy relies on host–guest interactions to
supramolecular polymers in which pillar[5]arene linked maintain short separations of chromophores while suppressing
anthracene-derived donors and acceptors by host-guest excitation energy quenching. Host–guest interaction using
interactions. The resulting water-dispersible nanoparticles bulky host, such as cucurbit[n]uril (n= 7, or 8), or pillar[n]arene
displayed efficient energy transfer and excellent light harvesting (n=5, or 6), has proved to be an effective approach to enhance
ability in part because the steric bulk of pillar[5]arene suppressed fluorescence intensity by encapsulating guest group of
self-quenching of the chromophores.
chromophoric molecules while hindering chromophores from
stacking.9 For example, Zhang and co-workers took advantage
of bulky CB[7] to suppress self-quenching of porphyrins and
constructed supramolecular photosensitizers with enhanced
antibacterial efficiency.9b However, to our knowledge only rare
examples of light-harvesting systems utilizing bulky hosts have
been reported to date.2b, 10 Below, we report a novel light-
harvesting system based on supramolecular polymeric
nanoparticles comprised of chromophoric guest molecules (GD
Photosynthesis starts with efficient absorption of sunlight by
the light-harvesting system. In it numerous peripheral antenna
chromophores are assembled together at well-defined
distance and orientation to guarantee that the excitation
energy is funneled directionally and rapidly to the acceptor of
the reaction centre.1 More than 200 organized chromophores
funnel energy into one acceptor, endowing the natural light-
harvesting system with considerable capacity to utilize solar
energy efficiently.1a Reported synthetic analogs of the light-
harvesting system used various scaffolds including
dendrimers,2 porphyrin arrays,3 organo or hydrogels,4
biopolymer assemblies5 and nanomaterials6. The development
and studies of these analogs have been motivated by the
and GA
) and disulfide-bridged bispillar[5]arene (bisP5A)
(Scheme 1). These water-dispersible supramolecular polymeric
fundamental
importance
of
understanding
natural
photosynthesis and potential applications in photocatalysis,
optoelectronic devices, and luminescent materials.7 However,
traditional
chromophores
are
vulnerable
to
photoluminescence quenching in these concentrated states.
Identifying strategies to maximize the density of
chromophores while minimizing self-quenching remain
a
critical but highly challenging task in the construction of
artificial light-harvesting system.7a, 8
Scheme
1
Chemical structures of disulfide-bridged
bispillar[5]arene (bisP5A), and the guest molecules (energy
donor: GD and energy acceptor: GA); cartoon representations
of bisP5A, GD, GA, their supramolecular polymers and the
light-harvesting supramolecular polymeric nanoparticles
(LHSPNPs); the schematic light-harvesting paths in the
LHSPNPs.
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nanoparticles (SPNPs) were prepared by the microemulsion
method from supramolecular polymers formed by host–guest
interaction of GD/GA and bisP5A. The formation of SPNPs
maintains the chromophores in close proximity of each other,
maximizing energy transfer and bulky pillar[5]arene minimizes
the self-quenching of excitation energy, leading to the
excellent light-harvesting ability.
We designed blue emissive diphenylanthracene derivative
(GD
)
as
energy
donor
and
green
emissive
diphenylethynylanthracene derivative (GA) as energy acceptor
(Scheme 1). GD and GA were synthesized in 5 steps with
overall yield of 47% and 37%, respectively (Scheme S1 and
Scheme S2 in ESI†). The large extinction coefficients (2.54 × 104
×
M-1 cm-1 for GD and 3.42 104 M-1 cm-1 for GA, Fig. S1a in
ESI†), well-separated absorption maxima (378 nm for GD and
450 nm for GA, Fig. S1b in ESI†), and significant spectral
overlap between the emission band of GD and the absorption
band of GA (Fig. S2 in ESI†, J=9.99 × 1014 M-1 cm-1 nm4) all
favour Förster resonance energy transfer.7a We modified both
diphenylanthracene and diphenylethynylanthracene with a
pair of cyanoalkyl triazoles to afford GD and GA respectively.
The motif of cyanoalkyl triazole has strong affinity towards
73 nm (Fig. 1c). Interestingly, under identical experimental
conditions GD alone formed nanosheets (NSs) as observed by
SEM (Fig. 1b). We speculate that the formation of these
nanosheets is driven by π–π stacking of diphenylanthracene
aromatic rings and hydrophobic interactions while host–guest
interactions are responsible for the supramolecular
polymerization of GD and bisP5A and the formation of SPNPs.
To further confirm the effect of pillar[5]arene and prove
that incorporation of GD into the bulky host suppresses self-
quenching, we compared the absorption and emission spectra
of GD in solution, in SPNPs and in NSs. In the first two systems,
individual GD molecules are isolated, whereas they are
assumed to be aggregated in NSs. As shown in Fig. 2a, the
absorption spectra of SPNPs and free GD in CHCl3 solution are
very similar, with the maximum absorption at 378 nm. In
contrast, the absorption spectrum of GD in NSs is
bathochromically shifted, with the maximum absorption at
410 nm, suggesting π–π stacking of the chromophores that is
absent in SPNPs. A similar effect was observed in fluorescence
spectra. Excitation of aqueous dispersions of SPNPs and NSs of
identical optical density resulted in ~4-fold higher emission
intensity from SPNPs compared to NSs (Fig. 2b). Their absolute
fluorescence quantum yields also demonstrate the difference:
4.3% for NSs, vs. 17.9% for SPNPs. Previously, SPNPs of the
pillar[5]arene with the binding constant of 1.2
CHCl3, driving the formation of the supramolecular polymers of
GD Pillararenes are emerging macrocyclic
GA and bisP5A 11
×
104 M-1 in
/
.
host with facile synthesis, unique rigid structure, versatile
functionalization, and interesting host–guest properties.12 We
here used disulfide-bridged bispillar[5]arene (bisP5A) because
of its convenient synthesis.13
The host–guest interactions were demonstrated by 1H
NMR and 2D ROESY spectroscopy. 1H NMR spectra of a
mixture of bisP5A and GD suggested the formation of
GD⊂bisP5A, as evidenced by upfield shifts of methylene
protons (Δδ1= -3.47 ppm, Δδ2= -2.90 ppm, Δδ3= -3.19 ppm,
Δδ4= -2.07 ppm, Fig. S3 in ESI†). The proton chemical shifts
1
described here were assigned on the basis of the H–1H COSY
spectrum (Fig. S4 in ESI†). The 2D ROESY spectrum showed
clear correlations between methylene protons of GD and
aromatic and methyl protons of bisP5A, further confirming this
inclusion complex (Fig. S5 in ESI†). The formation of
1
supramolecular polymers was probed by diffusion-ordered H
NMR spectroscopy (DOSY) and viscosity measurements. The
diffusion coefficients decreased from 4.99 × 10-10 to 1.28 × 10-
11
m2 s-1 as concentration of bisP5A and GD increased from 5
mM to 150 mM; the slope of double logarithmic plots of
specific viscosity vs. concentration increased from 1.09 to 1.99
as their concentration exceeded 12 mM (Fig. S6 in ESI†). Both
DOSY and viscosity measurements support the formation of
polymeric aggregates.
We prepared SPNPs from bisP5A and GD by the
microemulsion method.14 A 200 μL solution of bisP5A and GD
(both at 20 mM) in CHCl3 was injected into an aqueous
solution of cetyltrimethyl ammonium bromide (CTAB) followed
by ultrasonication for 25 min to afford nanospheres. Scanning
electron microscopy (SEM) revealed nanoparticles of regular
spherical shape and uniform size (Fig. 1a). Dynamic light
scattering (DLS) yielded an average hydro-dynamic diameter of
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same fluorophore linked by quadruple hydrogen bond
(Scheme S3 in ESI†) were reported to manifest fluorescence
quantum yield of 11.9%.15 We attribute the increased
quantum yield in these pillar[5]arene-based SPNPs to the
steric bulk of pillar[5]arene, whose outer diameter of 13.5 Å
(according to the minimized energy model of 1,4-
dimethoxypillar[5]arene (Fig. S7 in ESI†) and the X-ray crystal
structure of 1,4-dipropoxypillar[5]arene).16 In SPNPs, these
bulks disrupt π–π interactions, suppressing self-quenching and
enhancing emission.
Considering the advantage of SPNPs in preventing self-
quenching of aromatic chromophores, we constructed light-
harvesting supramolecular polymeric nanoparticles (LHSPNPs
)
by co-polymerization of bisP5A, GD, and GA. GA carried the
sample cyanoalkyl triazole complexing moiety and manifested
the same complexation with bisP5A as GD (Fig. S8 in ESI†). The
solubility of GA in CHCl3 was enhanced after the addition of
defined as antenna effect representing the degree of the
amplified GA emission assisted by the excitation of GD. In
addition, the excitation spectrum of LHSPNPs for 494 nm was
bisP5A, suggesting complexation of GA and bisP5A. BisP5A,
GA, and GD were first employed with ratio of 100: 2.0: 98.0 to
form ternary supramolecular polymers, which then assembled
into LHSPNPs. The participation of GA merely altered the
assembly behaviour and the ternary copolymers formed
spherical nanoparticles with a diameter similar to that of GD
and bisP5A pairs (~82 nm vs. ~73 nm, Fig. S9d and Fig. S9d’ in
ESI†).
nearly identical to the absorption spectrum of GD in SPNPs
,
proving that the excited energy of GA derives from absorption
of GD (Fig. S10 in ESI†).
Additional evidence for the energy transfer from GD to GA
was obtained from time-resolved fluorescence measurements.
We measured the lifetimes of the excited state of GD in binary
In LHSPNPs the fluorescence quenching of GD and
amplification of GA emission suggested the energy transfer
from donor GD to acceptor GA. When an aqueous dispersion
LHSPNPs was irradiated at 378 nm the emission of ternary
LHSPNPs at 430 nm decreased 69% compared to the emission
from a dispersion of binary SPNPs of the same optical density.
LHSPNPs also emitted at 494 nm, which corresponded to
fluorescence of GA (the green line in Fig. 3a). The 378 nm
excitation wavelength corresponds to the maximum extinction
SPNPs (GD + bisP5A) and ternary LHSPNPs (GD + GA + bisP5A)
of 1.3 ns and 0.8 ns, respectively (Fig. 4a). Such a prominent
shortening of the donor lifetime confirmed energy transfer
from GD to GA in the LHSPNPs. We also recorded time-
resolved fluorescence spectra of GA and GD in LHSPNPs with a
GA/GD ratio of 1.0:99.0 upon 375 nm excitation. We observed
a rapid increase in the fluorescence intensity of GD, followed
by the slower growth of GA emission (Fig. S12 in ESI†). Once
the emission peak of GD reached the maximum value (set as 0
ns), it began to decay while the emissive intensity of GA kept
increasing for 0.36 ns. (Fig. 4b). The spectral changes indicated
coefficients of GD and a negligible extinction coefficient of GA
.
In contrast, irradiating LHSPNPs at 450 nm, corresponding to
the maximum absorption of GA, produced emission intensity
at 494 nm 15-fold lower than that under 387 nm irradiation
(Fig. 3b). This difference in emission intensities from the same
fluorophore at different excitation wavelengths reflects two
factors: (a) a higher fraction of incident irradiation at 378 nm is
absorbed by LHSPNPs compared to 450 nm and (b) efficient
transfer of excitation energy from GD to GA. The value of 15
was determined by I494 nm (λ exc = 378 nm) /I494 nm (λ exc = 450 nm) and
the energy transfer from excited donor GD to acceptor GA
.
The obtained spectrum at 0.36 ns was similar with that of
LHSPNPs in the steady-state fluorescence measurements (the
blue line in Fig. 3a).
Increasing the GA/GD molar ratio from 0.5:99.5 to 3.0:97.0
increased the intensity of GA emission at 494 nm, while
decreasing the emission of GD at 430 nm (Fig. 3a). The
resulting energy transfer efficiency reaches the maximum of
85% at the GA
S3 in ESI†). In contrast, the antenna effect increased with the
decrease of the GA GD molar ratio (Fig. S13 and Table S2 in
/GD molar ratio of 3.0:97.0 (Table S2 and Table
/
ESI†) as more GD molecules transferred the excitation energy
to per GA chromophore reaching the maximum of 22 at the
GA
/GD molar ratio of 0.5:99.5.
In summary, we constructed novel light-harvesting
supramolecular polymeric nanoparticles, which were formed
by host–guest interactions between pillar[5]arene and
anthracene-derived energy donor (GA) and acceptor (GD).
Bulky pillar[5]arene inhibited self-quenching of these
chromophores while maximizing energy transfer from GD to
GA to afford highly emissive material. This strategy may inspire
Fig. 3 (a) Fluorescence spectra of aqueous dispersion of SPNPs
of GD and bisP5A and LHSPNPs with various GA/GD molar ratio
(λexc = 378 nm); (b) Fluorescence spectra of aqueous dispersion
of LHSPNPs excited by 378 nm and 450 nm (GA: GD = 2.0:98.0).
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We are grateful for the financial support from the National
Natural Science Foundation of China (21472202, 21525206,
21561130149, 21474124), and the 973 program
(2013CB933800).
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