A donor-acceptor type macrocycle: Toward photolyzable self-assembly

Article abstract of DOI:10.1039/d0cc01350a

A water-soluble macrocyclic host is reported, composed of alkoxyanthracene as the donor (D), and 4,4-bipyridinium as the acceptor (A). The intramolecular D-A structure renders the host highly photostable. However, the introduction of a strong electron-donating guest promotes the photodecomposition of alkoxyanthracene, yielding photolyzable host-guest complexes or aggregates.

Full text of DOI:10.1039/d0cc01350a

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A Donor-Acceptor Type Macrocycle: Toward Photolyzable Self-
Assembly
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Tian Tian,a Tingjuan Qian,a Tingting Jiang,a Yakui Deng,a Xiaopei Li,a Wei Yuan,a Yulan Chen,*a,b Yi-
Xuan Wang,*a,b and Wenping Hua,b
A water-soluble macrocyclic host is reported, composed of photodecomposable macrocycles for enriching the
alkoxyanthracene as donor (D), and 4,4-bipyridinium as acceptor photolyzable hostguest systems.
(A). Intramolecular D-A structure renders the host highly
photostable. However, the introduction of strong electron- photodegradable materials has been proposed, that is,
donating guest promotes the photodecomposition of supramolecular self-assembly induced
photolysis.6
alkoxyanthracene, yielding photolyzable hostguest complexes or Alkoxyanthracene derivatives were selected as the
In our previous work, a new strategy for construction of
aggregates.
photolyzable guests,7 and their photo-reactivities were
enhanced upon addition of macrocycles, yielding highly
photoactive assemblies. Inspired by the success, a potentially
photolyzable and water-soluble macrocycle (AnMV) was
designed and synthesized, which consists of a photo-responsive
alkoxyanthracene (An) unit and a dicationic 4,4-bipyridinium
(MV) unit (Scheme 1). The electron-deficient MV, which is
closely anchored within the macrocycle, extinguished the
photoactivity of An, making the macrocyclic host photo-inert.
Moreover, the introduction of strong electron-donating guest
replaced the intramolecular donor (D)-acceptor (A) interaction
with the intermolecular D-A interaction, and thereby freed An
unit for efficient photodecomposition. Additionally, hostguest
nanoaggregate on the basis of AnMV can be fabricated by
altering the hydrophilicity of guest. The present study provides
pioneering proof of principle for smart self-assembly systems
based on photolyzable macrocyclic hosts, which will show great
potential in photosynthesis and targeted therapeutics.8a
The development of photo-decomposable structure had
derived a series of degradable materials,1 and targeted delivery
vehicles.2 Supramolecular self-assembly based on macrocyclic
compound possessed the inherent advantage in the fabrication
of photodegradable systems. The non-covalent binding,
between macrocyclic host and guest molecule, makes the
association highly dynamic, which can be easily disrupted.
Numerous hostguest pairs have been employed in
photodegradable systems, most of which rely on photoactive
guests and traditional macrocycles.3 However, such systems
may not show the complete photolysis because most
macrocycles are reserved after irradiation, which can bind with
decomposed guests to form new assemblies. Meanwhile,
photo-responsive macrocyclic hosts have not been fully
developed due to the complicated synthesis, and the steric
inhibition of photo-isomerization by ring strain and molecular
crowding.4 Hence, the development of the macrocyclic
compounds with efficient photoreactivity has become an
urgent requirement for photodegradable supramolecular
systems. Recently, macrocyclic hosts based on photo-
isomerized bridging subunits were developed, which showed
excellent photo-controlled guest release.5 As a matter of fact,
there also reminded a need for the development of thoroughly
a. Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of
Chemistry, School of Science, Tianjin University, Tianjin 300072, China
E-mail: yulan.chen@tju.edu.cn, yx_wang@tju.edu.cn
b. Collaborative Innovation Center of Chemical Science and Engineering (Tianjin),
Tianjin 300072, P. R. China
Scheme 1. Self-assembly modes of AnMV with different guests,
and the chemical structures of all the substances in this work.
† Electronic Supplementary Information (ESI) available.
See DOI: 10.1039/x0xx00000x
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1,3,6,8-Pyrenetetrasulfonic acid tetrasodium salt (PTS) was shifts for the same reason. As a control, protons of MV units in
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DOI: 10.1039/D0CC01350A
selected to be the guest molecule because it can be easily acyclic MVOH underwent smaller upfield resonance shifts with
associated with positively charged AnMV, and its strong PTS (Figure S4), again indicating the weaker interaction
electron-donating ability is beneficial to mediate the D-A between PTS and MVOH. Job plot was obtained to determine
interaction.9 UVvis absorption spectroscopy was performed to the binding stoichiometry. A peak at the molar fraction of 0.5
monitor the D-A interaction of the hostguest system. It was was observed (Figures S5), verifying a 1:1 (or n:n) binding
clearly shown in Figure 1a that AnMV and AnMVPTS had between AnMV and PTS.14 The diffusion coefficients of
distinctly different absorption band between 500 nm and 700 AnMVPTS complex, AnMV and PTS were measured by the
nm, providing the evidence for the forming of new CT diffusion-ordered spectroscopy (DOSY). When PTS was added
interaction between PTS and AnMV.8a Compared with the to AnMV aqueous solution, the diffusion coefficient was
AnMV (max = 525 nm), the maximum absorption band of decreased from 2.88 × 10-10 to 2.00 × 10-10 m2s-1, and protons
AnMVPTS complex exhibited a bathochromic shift (max = 550 from both components showed similar coefficients, meaning
nm) with increased intensity, indicating that the CT interaction that one primary complex was formed with slower diffusion
of AnMVPTS complex was stronger than that of AnMV itself.10 (Table S1). According to the Stokes-Einstein equation, the
Such spectral change can also be easily observed by naked eye hydrodynamic volume of AnMV was only increased by 2.90
(Figure S1). On the contrary, the noncyclic control compound, times after addition of PTS,15 which can preclude the possibility
MVOH, did not show CT absorption above 500 nm in the of n:n AnMVPTS aggregation. Therefore, we can confirm a 1:1
presence of PTS, implying that the regulation of D-A interaction binding stoichiometry for AnMVPTS complex in solution.
1
cannot be achieved without macrocyclic structure. Furthermore, binding affinity was quantitively studied via H
Fluorescence spectroscopy was also used to testify the NMR titration experiment. The association constant (Ka) is
evolution of D-A interactions.11 The emission intensity of PTS determined, by the nonlinear curve simulation, as (4.77  0.35)
was decreased by 80% after binding with AnMV (Figure 1b),  104 M-1 (Figures S6), which illustrated the strong binding
ascribed to the photo electron transfer (PET) between PTS and ability of AnMV to PTS. 2,6-Naphthalenedisulfonic acid
MV unit.12 Meanwhile, only 32% of fluorescence was quenched disodium salt (NDS) was also selected as a guest for AnMV to
with MVOH, again revealing the essential role of macrocyclic study the effect of guest structure on hostguest complexation.
structure in the intermolecular interaction. We further As shown in Figure S7, the CT absorption of AnMV only slightly
demonstrated the formation of AnMVPTS complex by cyclic changed when a large amount of NDS was added, implying a
voltammetry experiments. As shown in Figure S2a, redox peaks much less sufficient regulation on CT interaction by NDS. A
of MV moieties in AnMVPTS complex were different with significant decrease in the association constant was also found
those in free AnMV. However, redox peaks of MVOH had (Ka = (154  25) M-1 for AnMVNDS complex, Figure S8),
almost no change in the presence of PTS, suggesting that the suggesting that smaller aromatic core of guest molecule might
electrostatic interaction between MVOH and PTS was too weak significantly reduce the association ability.5a
to yield CT complex (Figure S2b). All these results proved that
the PTS was successfully incorporated with cyclic AnMV, and
replaced the intramolecular CT interaction of AnMV itself with
the intermolecular CT interaction between AnMV and PTS.
1
Figure 2. Partial H NMR spectra of PTS, AnMVPTS complex,
Figure 1. (a) UVvis absorption spectra, and (b) fluorescence
and AnMV (400 MHZ, 0.5 mM).
spectra (ex = 365 nm) of PTS, AnMVPTS, AnMV, MVOH, and
MVOHPTS in water. The concentrations of all the constituents
were 0.5 mM in UVvis experiments, and 0.01 mM in
fluorescence experiments.
2D NOESY NMR spectrum was further utilized to explore the
binding geometry of AnMV with PTS. The NOE correlation of H
of PTS with H3 of the glycol chain, and correlations of H of PTS
with protons of An and MV, were clearly observed (Figure S9b
NMR experiments were performed for detailed information
and S9c), jointly suggesting that the pyrene segment was
about the hostguest binding behavior in the solution state.
Compared with those in free AnMV, all the protons of AnMV
underwent upfield resonance shifts in the presence of PTS
(Figure 2a), due to the ring current effect of the aromatic nuclei
embedded in the macrocycle, and was oriented parallelly with
the MV segment. Combined with the conclusions from 1D NMR
experiments, the geometric structure of complex was deduced
(Figure S9d,e), which was further verified by DFT calculations
of pyrene, confirming the spatial correlation between two
(Figure S10). The complexation in the solid state was also
components.10,13 The PTS protons also showed visible upfield
studied by XRD analysis of the single crystal of 1:1 AnMVPTS
2 | J. Name., 2012, 00, 1-3
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complex. As displayed in Figure 3, PTS was located between MV donating ability of guest facilitated the photoactivity of the
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and An units of the host, and adopted a parallel arrangement to hostguest complex. The photolytic prodDuOctI:s1o0f.1f0r3e9e/DA0nCMC0V13a5n0dA
MV, which revealed the mechanism of the regulation on AnMVPTS complex were identified by 1H NMR, GC-MS and HR-
intramolecular CT interaction by hostguest binding.16 The EI-MS measurements. The irradiated mixture was purified via
close association (ca. 2.3 Å) of oxygen atoms of PTS with Hc/Hd solvent extraction, and the results were consistent with those
of glycol chain and Ha of MV was observed, resulting from the of proposed products (Figures S13S15). It fully proved that
electrostatic interaction between sulfonate group and AnMV underwent same photo-transformation as reported in
pyridinium.17 Although pyrene was not fully embedded into the the presence and absence of PTS, and excluded the possibility
macrocyclic cavity in the densely packed crystal state, it is that the changes in photo-activity were derived from different
possible that PTS can be included into AnMV in the more reaction routes. In the light of results, we could conclude that a
flexible solution state in terms of their sizes and shapes.18
photostable macrocyclic host was successfully developed
because of the efficient intramolecular CT interaction. The
introduction of highly electron-rich guest inhibited the PET
process from An to MV segments in host, and further enabled
the photo-reactivity, making the hostguest complex
photolyzable. Note that the specific signals of PTS in aqueous
solution were observed after irradiation (Figure S16), implying
that PTS was not destroyed during the photo-reaction.
Therefore, such hostguest system could be potentially used as
photo-degradable inclusion, which was widely applied in
biotechnology and pharmacy.20
Figure 3. Solid-state (super)structure of AnMVPTS complex
obtained from X-ray crystallography on single crystal. The
counterions and solvent molecules are omitted for the sake of
clarity.
Combining all the results, we can conclude that there is CT
interaction in AnMV itself, in which An units is the electron
donor and MV group is the electron-acceptor. The addition of
strong electron-donating guest will regulate the CT interaction
through the encapsulation by macrocycle driven by
electrostatic interaction.
Figure 4. (a) Normalized absorbance at 405 nm of the free
AnMV, and AnMVPTS complex upon irradiation at 365 nm for
different times. Error bars indicate SDs from three
measurements for each point. (b) The intensities of dynamic
laser scattering (DLS) light of AnMVPS aggregates before and
after irradiation. Inset: DLS data of AnMVPS aggregate in
water. Concentrations of all the substances were kept at 0.1
mM.
9,10-Alkoxyanthracene is a typical photolytic unit.7 It can be
converted to endoperoxide (EPO) by singlet oxygen, generated
from triplet oxygen under irradiation, and further decompose
into 9,10-anthraquinone.8a The reactivity was highly dependent
on the electron density of anthracene.19 Herein, An unit in
AnMV should be optically stable due to the D-A structure, but
be photo-responsive with the electron-donating guest. UVvis
absorption at 405 nm was recorded to monitor the photolysis
of AnMV and its hostguest complex, as PTS did not show
intense absorption at this wavelength both before and after
irradiation (Figure S11a). As shown in Figures 4a and S11b, the
absorption of AnMV had almost no change after irradiation for
60 min, indicating the excellent photo-stability. In contrast, the
absorption of AnMVPTS complex at 405 nm decreased by 77%
under the same condition. According to the Ka, 64% of AnMV
was bound with PTS at the experimental concentration.
Therefore, all the complexed AnMV had been decomposed,
manifesting that the complex is highly photoactive. NDS was
also tested as the guest molecule for comparison. As the Ka of
AnMVNDS complex was much smaller than that of AnMVPTS
complex, we used excess NDS to ensure the high complexation
degree of AnMV. After addition of 500 eq of NDS, 88% of AnMV
was complexed, but only 56% of AnMV was photo-decomposed
(Figure S12). It clearly demonstrated that stronger electron-
Stimulus-responsive nanoaggregates can be constructed by
hostguest complexation, which have a wide range of
application in environmental science, and biomedicine.21 To our
particular interest herein is that, 1:1 (molar ratio) mixture of
AnMV and 1-pyrenesulfonic acid sodium salt (PS) in aqueous
solution showed the Tyndall effect (Figure S17), which
promoted us to explore the aggregation based on this
hostguest self-assembly system. The critical aggregation
concentration (CAC) of AnMV (0.15 mM) in the presence of PS
was measured by monitoring the dependence of the optical
transmittance at 710 nm on PS concentration. The optical
transmittance decreased gradually as the concentration of PS
increased because of the scattering effect of newly formed
nanoscale assembly (Figure S18a), and the CAC was obtained as
ca. 0.08 mM (Figures S18b). However, the optical transmittance
of AnMV without PS at 710 nm showed no appreciable change
as the concentration increased from 0.05 to 0.25 mM (Figure
S19). Due to less sulfonate groups attached on pyrene core, PS
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J. Name., 2013, 00, 1-3 | 3
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was more hydrophobic and was easier to stack than PTS, which
leads to the complexation-induced aggregation.22 Furthermore,
dynamic laser scattering (DLS) and scanning electron
microscope (SEM) were employed to identify the morphology
of AnMVPS assembly. DLS result showed that AnMVPS
complex formed aggregates with a narrow size distribution,
giving an average diameter of 328 nm (Figure 4b). The SEM
image (Figure S20a) revealed that the aggregates were
nanospheres. We further explored the photodegradation of the
supramolecular assembly. The UVvis absorption of AnMVPS
assembly at 405 nm decreased significantly after irradiation
4
5
6
7
8
(Figures
S21
and
S22),
implying
the
efficient
photodecompositon of AnMV in aggregate. The CT band for
AnMVPS complex showed a bathochromic shift with increased
intensity, indicating that the photolysis was also because of the
mediation on CT interaction of AnMV. In addition, the intensity
of scattering light of aggregate pronouncedly decreased (Figure
4b), demonstrating the size and quantity of nanoaggregates
were reduced. The spherical assemblies also disappeared in the
SEM image (Figure S20b). We also Hence, we successfully
constructed photodegradable nanoaggregates based on
hostguest chemistry of AnMV.
9
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In conclusion, a water-soluble macrocycle, AnMV, was
designed and synthesized. The intramolecular D-A structure
lowered the electron density of An segment, making AnMV
photo-stable. However, when a strongly electron-donating
guest (e.g., PTS) was introduced, it was embedded into the
macrocyclic host, leading to increased electron density on An
unit and considerably enhanced photo-decomposition of the
complex. By adjusting the hydrophilicity of guest molecule, we
could also obtain photodegradable nanoaggregates
(AnMVPS). This hostguest system provides a new train of
thought for photo-responsive self-assemblies, and exhibits
promising applications for photo-controlled drug delivery and
molecular switching in the future.
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Figure S3.
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This work was supported by the National Key Research and
Development Program of China (Grants 2016YFB0401100) and
the National Natural Science Foundation of China (Grants
21604062). The authors are grateful to Prof. Long Chen (Tianjin
University) for his help with photoreaction measurements.
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Conflicts of interest
There are no conflicts to declare.
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DOI: 10.1039/D0CC01350A
Tittle: A Donor-Acceptor Type Macrocycle: Toward Photolyzable Self-Assembly
Description: A donor-acceptor macrocyclic host is reported, which showed efficient
photodecomposition with electron-donating guests, yielding photolyzable host-guest
complexes or aggregates.
Graph: