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Bioinspired Molecular Design of Light-Harvesting Multiporphyrin Arrays.

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T. Aida et al.
Artificial Photosynthesis
Bioinspired Molecular Design of Light-Harvesting
Multiporphyrin Arrays
Myung-Seok Choi, Tomoko Yamazaki, Iwao Yamazaki, and Takuzo Aida*
Keywords:
dendrimers · energy transfer · light harvesting ·
photosynthesis · porphyrinoids
R
ecent progress in fundamental studies on multiporphyrin arrays has
provided structural parameters for the molecular design of artificial
light-harvesting antennae which mimic the wheel-like antenna
complexes of photosynthetic purple bacteria. Covalent and noncovalent approaches have been employed for the construction of artificial
light-harvesting multiporphyrin arrays. Such arrays are categorized
into ring-shaped, windmill-shaped, star-shaped, and dendritic architectures. In particular, dendritic multiporphyrin arrays have been
proven to be promising candidates for both providing a large
absorption cross-section and enabling the vectorial transfer of energy
over a long distance to a designated point. Such molecular and
supramolecular systems are also expected to be potent components for
molecular electronics and photonic devices.
1. Introduction
Biological photosynthesis is one of the most interesting
photochemical events and converts solar energy into chemical
potentials. The crystal structures of some of the light-harvesting antenna complexes present in purple photosynthetic
bacteria show the presence of highly symmetric wheel-like
supramolecular architectures involving a great number of
bacteriochlorophyll pigments (Figure 1).[1] Such wheel-like
chromophore arrays play an essential role in the efficient
capturing of light energy and its subsequent funneling to the
reaction center.[2] These structural features have motivated
chemists to design artificial light-harvesting antennae consisting of multiple porphyrin units and to explore their
photochemical properties so as to generate a general ap-
proach for achieving the vectorial
transfer of energy over a long distance
to a designated point. Such synthetic
light-harvesting antenna molecules not
only contribute to a better understanding of the photochemical events involved in biological photosynthesis,
but also have a great potential as
nanoscopic objects for molecular electronics and photonics
involving photovoltaic cells, field-effect transistors, and lightemitting devices.[3]
Herein we focus on a recent development of covalent
(molecular) and noncovalent (supramolecular) approaches to
[*] Dr. M.-S. Choi, Prof. Dr. T. Aida
ERATO Nanospace Project
Japan Science and Technology Corporation (JST)
2-41 Aomi, Koto-ku, Tokyo 115-0064 (Japan)
Fax: (+ 81) 3-5841-7310
E-mail: aida@macro.t.u-tokyo.ac.jp
Dr. T. Yamazaki, Prof. Dr. I. Yamazaki
Department of Chemical Process Engineering
Graduate School of Engineering
Hokkaido University
Kita-13-Nishi-8, Kita-ku, Sapporo 060-8628 (Japan)
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Figure 1. Schematic representation of the active site of purple photosynthetic bacteria.
DOI: 10.1002/anie.200301665
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Light-Harvesting Multiporphyrin Arrays
the design of light-harvesting multiporphyrin arrays including
1) ring-shaped, 2) star-shaped, 3) windmill-shaped, and
4) dendritic architectures, where special emphasis is placed
on their geometry-dependent photochemical properties.
which the PZn-to-PFB energy transfer rate constant (kENT) and
the quantum efficiency (FENT) have been evaluated to be
2.9 4 1010 s 1 and 99 %, respectively. In contrast, cyclic hexamer 2, which consists of five PZn units and a single PFB unit,
2. Ring-Shaped Light-harvesting Antennae
Ring-shaped multiporphyrin arrays[4] are interesting candidates for artificial light-harvesting antennae which are
intended to mimic structural aspects of the wheel-like
chromophore arrays in photosynthetic purple bacteria. Cyclic
hexamer 1, which consists of an alternating arrangement of
zinc and free-base porphyrins (PZn and PFB), has been
synthesized by a Pd-mediated coupling of a zinc complex of
bis(4-ethynylphenyl)porphyrin and a free-base bis(3-iodophenyl)porphyrin in the presence of a template molecule.[5]
Time-resolved spectroscopy has shown that the photoexcited
singlet state of the PZn units has a lifetime (t) of 17 ps, from
shows a FENT value of only 40 %.[6] Although the advantages
of such ring-shaped chromophore arrays over linear analogues in intramolecular energy transfer have been discussed
in the literature,[7] the realization of vectorial energy transfer
along the ring system still remains a challenge.
3. Star-Shaped Light-Harvesting Antennae
Star-shaped porphyrin pentamers consisting of a focal
free-base porphyrin unit (PFB) attached to four peripheral zinc
Takuzo Aida was born in 1956. He received
his Ph.D. from the University of Tokyo in
Polymer Chemistry in 1984, and then began
an academic career at the University of Tokyo. In 1996, he was promoted to Full Professor at the Department of Chemistry and
Biotechnology at the University of Tokyo.
His research interests include controlled
macromolecular synthesis with mesoporous
inorganic materials, photo- and
supramolecular chemistry of dendritic macromolecules, fabrication of nanoscopic materials, and bio-related molecular
recognitions and catalyses. In 1996, he was appointed as a researcher of
the JST PRESTO Project “Fields and Reactions”, and in 2000 was the
leader of the ERATO Project on “NANOSPACE”.
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Myung-Seok Choi was born in 1968 in Korea. He received his Ph.D. from the University of Tokyo in 2002. He then joined the
ERATO Nanospace Project, Japan Science
and Technology Corporation (JST). In 2003,
he joined the Fusion Domain Laboratory of
the SONY Cooperation. His research interests focus on the design of dendritic macromolecules by using molecular and
supramolecular approaches.
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porphyrin units (PZn) have been extensively studied as
simple models of biological light-harvesting antennae.
Compound 3 is an early example of a multiporphyrin
array that makes use of diphenylethyne spacers for the
connection of PFB and PZn units with a center-to-center
distance of 20 :.[8] The PZn-to-PFB energy transfer efficiency
(FENT) in 3 has been reported to be 90 %, with a weak
electronic donor–acceptor interaction at the ground state
playing a role.[9] Compound 4 containing flexible nucleosidic
spacers between energy donor and acceptor units has been
synthesized. Interestingly, the flexible linkers allow the
PZn units to wrap around and electronically shield the
PFB unit. Nevertheless, steady-state fluorescence spectroscopy
studies have shown that compound 4 displays essentially
identical PZn-to-PFB energy-transfer characteristics as compound 3.[10]
Inclusion complex 5, which consists of a tetrakis(4pyridyl)porphyrin free base (PFB) surrounded by a rigid cyclic
tetramer of zinc porphyrin (PZn) has been synthesized.[11, 12]
Photoexcitation of 5 at 411 nm results predominantly in
electron transfer from the PZn units to the included PFB molecule, where the fluorescence from the peripheral PZn units is
quenched without any enhancement of the emission from the
PFB molecule. In sharp contrast, photoexcitation of the
PZn units of inclusion complex 6, which has a rigid coordina-
Iwao Yamazaki was born in 1942. He received his Ph.D. from Hokkaido University
in Molecular Photophysics in 1972, and
then joined Hokkaido University as an Assistant Professor. In 1980, he moved to the Institute of Molecular Science (Okazaki,
Japan) as an Associate Professor, and then
joined Hokkaido University in 1988 as a
Full Professor at the Department of
Chemistry. His research interests include ultrafast photochemical processes in organized
molecular systems and their applications to
quantum mechanical switching devices. In
1990 he received the Distinguished Research Award, Chemical Society of
Japan in the field of time-resolved spectroscopy of molecular photophysics.
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Tomoko Yamazaki was born in 1945. She
graduated from Hokkaido University (Faculty of Pharmacy), and then joined the Research Institute of Applied Electricity at
Hokkaido University as a Research Assistant. In 1980–1988 she was involved in
time-resolved fluorescence studies on molecular assemblies at the Institute of Molecular
Science. In 1988 she returned to Hokkaido
University.
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Light-Harvesting Multiporphyrin Arrays
tion square consisting of four PZn units and an internal
PFB unit, shows an enhancement in the fluorescence from
the PFB unit at the expense of that from the PZn units. This
effect occurs as a result of a PZn-to-PFB energy transfer.[13] A
ruthenium porphyrin (PRu) forms a side-to-face assembly 7
4. Windmill-Shaped Light-Harvesting Antennae
The synthesis and photochemical properties of windmillshaped multiporphyrin arrays have been investigated; their
molecular structures, though essentially similar to star-shaped
architectures, possibly would allow incorporation of a larger
number of chromophore units, thereby increasing the absorption cross-section. Windmill-like multiple zinc-porphyrin
arrays with a meso-meso-coupled zinc porphyrin (PZn) dimer
(9, n = 1, 2) at its center have been synthesized, as well as their
with a tetrakis(4-pyridyl)porphyrin (PFB) free base through
axial coordination interactions.[14] The photoexcited singlet
state of the PRu units is strongly perturbed by the heavy metal
effect of the Ru atoms,[15] which results in a highly efficient
intersystem crossing to the triplet state (100 % efficiency).
Excitation of compound 7 at 532 nm results in a PRu-to-PFB
energy transfer via the triplet state occurring with 100 %
efficiency and a kENT value in the range of 108–109 s 1.[16]
Compound 8 is also an interesting multiporphyrin array
because of its unique three-dimensional supramolecular
architecture formed through cooperative coordination interactions.[17] The kENT and FENT values of 8 have been evaluated
by time-resolved fluorescence spectroscopy to be 2 4 109 s 1
and 73 %, respectively.
Star-shaped multiporphyrin arrays are therefore potent
candidates for highly efficient energy transfer. However, the
number of chromophore units that can be incorporated into
those molecules is only small, thus, preventing the formation
of a large absorption cross-section, which is essential for
capturing low numbers of photons.
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polymeric homologues (gridlike architecture).[18, 19] The focal PZn dimer in 9 has a
slightly lower energy (2.08 eV) than those
at the periphery (2.15 eV), thereby allowing
the excitation energy to flow from the
periphery to the central core. In fact,
photoexcitation of 9 at 540 nm (nonselective excitation) results in an enhanced
emission from the meso-meso-linked PZn
units (651 nm) at the expense of the fluorescence from the peripheral PZn units (580
and 629 nm). Time-resolved spectroscopy
has shown that 9 has biphasic fluorescence
decay behavior, which is composed of two
exponential components with lifetimes of
56 ps (73 %) and 1.62 ns (27 %) which are
assignable to the decays of the peripheral
and core PZn units, respectively. The timeresolved spectra at the initial stage consist
predominantly of an emission from the
peripheral PZn units which is then transformed rapidly to a broad emission from the
focal PZn dimer. The photochemical properties of a novel electron-transfer relay system consisting of acceptor-appended 9 (n =
1) have also been reported.[20]
5. Dendritic Light-Harvesting
Antennae
In general, energy-transfer properties by a through-space
(F@rster) mechanism are dependent on the donor–acceptor
(D-A) distance r, where the efficiency would decrease
according to 1/r6.[21] Artificial light-harvesting antennae
require a great number of chromophore units to obtain a
large absorption cross-section.[22] Dendrimers are hyperbranched, three-dimensional macromolecules with regular
treelike arrays of branch units,[23] and have attracted great
attention as novel nanoscopic light-harvesting molecules.[24]
Hence, dendritic architectures are interesting scaffolds for the
three-dimensional positioning of a great number of chromophore units. However, if these chromophore units do not
cooperate with one another, the acquired light energy is
scattered and the excited states are lost before the energy is
channeled to a designated functionality, which triggers, for
example, electron-transfer reactions. Therefore, the molecular design of energy funnels should be considered for the
vectorial transfer of energy over a large distance.
Examples of dendritic multiporphyrin arrays include a
vinylene-linked nonameric dendritic nickel porphyrin array[25]
and a nonameric dendritic zinc porphyrin array with ethynylene and ester spacers.[26] Compound 10, which consists of an
energy-accepting free-base porphyrin (PFB) core decorated
with eight energy-donating zinc porphyrin (PZn) units, was
later synthesized for photochemical studies.[27] Excitation of
the PZn units of 10 results in fluorescence emission from the
PFB focal core as a result of a PZn-to-PFB energy transfer.
Evaluation of the fluorescence decay profile of the PZn units
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shows that the energy transfer takes place rather slowly
(kENT = 9 4 108 s 1) with a quantum efficiency (FENT) of 60 %.
The fluorescence quantum yield of the PFB core in compound
10 is virtually identical to that of the model porphyrin
monomer.
The synthesis of a metalloporphyrin array consisting of
21 nickel porphyrin units, referred to as mandala-patterned
bandanna, has been reported, whose energy-transfer properties, however, were not investigated because of the photochemical inertness inherent to nickel porphyrin derivatives.[28]
However, the photoactive dendritic multiporphyrin array 11,
which consists of 21 porphyrin units attached through diarylethyne linkers to a free-base porphyrin focal core, has been
synthesized.[29] Time-resolved absorption spectroscopy of
compound 11 has shown a decay of the excited singlet state
of the PZn units, followed by an increase in the absorption of
the PFB core. The PZn-to-PFB energy transfer has a FENT value
of 92 %.
Energy-transfer events on the dendrimer surface are also
interesting. This prompted the synthesis of dendritic poly(llysine) 12, which bears two hemispherically segregated
domains comprised of 16 free-base porphyrin (PFB) units
and 16 zinc porphyrin (PZn) units on the exterior surface. A
steady-state fluorescence study has shown the occurrence of a
two-dimensional PZn-to-PFB energy transfer with a FENT value
of 43 %.[30] Here, photoexcitation of a certain PZn unit in
compound 12 is followed by an energy migration within the
PZn domain, and then the excitation energy is transferred to a
PFB unit at a boundary of the two domains.
The large dendritic multiporphyrin array 13 a has been
synthesized. This array consists of four dendritic wedges of a
zinc porphyrin heptamer (7PZn), which act as energy donating
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units, that are anchored by a free-base porphyrin (PFB) focal
core, which acts as the energy acceptor.[31] This molecule is
intended to mimic the morphologies of wheel-like supramolecular assemblies of bacteriochlorophyll pigments in
biological light-harvesting antennae. Excitation of the PZn units in compound 13 a results in a highly efficient PZn-to-PFB
energy transfer that generates an enhanced emission from the
PFB focal core. In sharp contrast, compound 14 a, a conical
version of 13 a, displays an emission mostly from the PZn units,
Angew. Chem. Int. Ed. 2004, 43, 150 –158
with only a weak emission from the PFB focal core.
Time-resolved fluorescence spectroscopy of 13 a initially shows an increase in the fluorescence from the
PZn units (589 and 637 nm), which then decays progressively to allow the generation of a new fluorescence
from the PFB core. The average lifetime of the photoexcited PZn units in compound 13 a (680 ps) is much
shorter than those in compound 14 a (1899 ps), despite
the fact that 13 a has a large number of PZn units located
away from the energy-accepting PFB focal core. The
energy transfer rate constant (kENT) for 13 a has been
evaluated to be 1.04 4 109 s 1, which is one order of
magnitude larger than that for 14 a (0.10 4 109 s 1). The
energy-transfer efficiencies (FENT), calculated from
these kENT values, are 71 and 19 % for 13 a and 14 a,
respectively, which have very different structures. This
observation indicates the important role of the morphology of
the chromophore array in intramolecular energy transfer. A
fluorescence depolarization study has shown that the energy
transfer in 13 a is facilitated by a cooperative energy migration
among the dendritic PZn units, a situation analogous to the
photochemical events in bacterial light-harvesting antenna
complexes.
Photochemical properties of two series of dendritic
compounds 13 a–c and 14 a–c show very different depend-
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encies on the generation number.[32] The FENT value decreased from 86 % (14 c) to 66 % (14 b), and then to 19 %
(14 a), while the energy-transfer properties of 13 a–c with four
dendritic zinc porphyrin wedges exhibit a much smaller
generation-number dependency: FENT value ranges from
87 % (13 c) to 80 % (13 b), and then to 71 % (13 a). Lightharvesting activities of the multiporphyrin arrays can be
evaluated from the molar extinction coefficients (e415) of the
Soret absorption band (l = 415 nm) multiplied by the PZn-toPFB energy transfer efficiency (FENT). The light-harvesting
activity of 13 a–c is considerably increased with increasing
generation number of the dendritic wedges; the e415 FENT value of 13 a, for example, is ten times as large as that of 14 c. In
sharp contrast, those values for compounds 14 a–c are much
lower and hardly dependent on the generation number.
Dendritic light-harvesting antennae, like biological lightharvesting antennae, also require a certain molecular geometry to enhance the energy-transfer activities.
Supramolecular versions of dendrimer-like light-harvesting complexes have been reported. A hydrogen-bonded zinc
porphyrin cyclic dimer (2PZn) forms nonameric and heptadecameric multiporphyrin arrays (15 a)[33, 34] through metal–
ligand coordination with a free-base porphyrin focal core
bearing pyrazine arms (PFB). Energy transfer takes place with
a FENT value of 80 % upon excitation of the 2PZn units, which
results in a fluorescence emission from the PFB focal core.[34]
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On the other hand, serial-type compound 15 b shows a lessefficient energy transfer with a FENT value of only 55 %.
These contrasting values indicate an important role of the
geometry of 15 a in the efficient transfer of energy.
6. Summary and Outlook
Artificial photosynthesis is one of the ultimate goals of
science and technology for the 21st century. Artificial photosynthesis can be realized by the integration of light-harvesting
antenna parts with an electron-transfer relay system that
enables long-lived charge separation. Artificial light-harvesting antennae require a molecular design that allows incorporation of a great number of chromophore units to obtain a
large absorption cross-section for capturing a low number of
photons. At the same time, those chromophore units are
required to cooperate efficiently with one another so as to
channel the acquired light energy over a long distance to a
designated point. A three-dimensional molecular design of
chromophore arrays is essential for an efficient cooperation
of chromophore units. The highlighted multiporphyrin arrays
for capturing visible light are roughly classified into four
categories, depending on their molecular geometries. Among
those, dendritic scaffolds appear to be the most promising for
the three-dimensional arrangement of a large number of
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Light-Harvesting Multiporphyrin Arrays
chromophore molecules and also for an efficient cooperation
of those chromophore molecules to act as energy funnels and
allow vectorial energy transfer. Future research along this line
would also involve integration of these artificial antennae into
electron-transfer relay systems to achieve artificial photosynthesis. Furthermore, their potential applications also include
solar cells, light-emitting materials, sensor systems, and many
other electronic and photonic nanodevices that utilize the
conversion of light energy into chemical potentials.
[19]
[20]
[21]
[22]
Received: May 2, 2003 [M1665]
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multiporphyrin, design, molecular, bioinspired, array, light, harvesting
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