Porphyrin Antennas on Carbon Nanodots: Excited State Energy and Electron Transduction

Article abstract of DOI:10.1002/anie.201704544

We report the synthesis and electron donor–acceptor features of a novel nanohybrid, in which the light-harvesting and electron-donating properties of a meso-tetraarylporphyrin (TArP) are combined with the electron-accepting features of nitrogen-doped carbon nanodots (NCNDs). In particular, in an ultrafast process (>10¹² s^?1), visible-light excitation transforms the strongly quenched porphyrin singlet excited states into short-lived (225 ps) charge-separated states. On the other hand, ultraviolet light excitation triggers a non-resolvable transduction of singlet excited state energy from the NCNDs to the porphyrins, followed by the same charge separation observed upon visible light excitation.

Full text of DOI:10.1002/anie.201704544

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Accepted Article
Title: Porphyrin Antennas on Carbon Nanodots: Excited State Energy
and Electron Transduction
Authors: Maurizio Prato, Francesca Arcudi, Volker Strauss, Luka
Dordevic, Alejandro Cadranel, and Dirk Guldi
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201704544
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Porphyrin Antennas on Carbon Nanodots: Excited State Energy
and Electron Transduction
Francesca Arcudi,[a] Volker Strauss,[b] Luka Đorđević,[a] Alejandro Cadranel,[b] Dirk M. Guldi,*[b] and
Maurizio Prato*[a,c,d]
Dedicated to Professor Renato Noto on the occasion of his retirement
Abstract: We report the synthesis and electron donor-acceptor
features of a novel nano-hybrid, in which the light harvesting and
electron donating properties of a meso-tetraarylporphyrin (TArP) are
combined with the electron accepting features of Nitrogen-Doped
Carbon Nanodots (NCNDs). In particular, in an ultrafast process (>
1012 s-1), visible light excitation transforms the strongly quenched
porphyrin singlet excited states into 225 ps lived charge separated
states. On the other hand, ultraviolet light excitation triggers a non-
resolvable transduction of singlet excited state energy from the
NCNDs to the porphyrins, followed by the same charge separation
observed upon visible light excitation.
nanohybrids.[20] Given their remarkable charge-transfer activity,
there is no doubt about the potential of CNDs as valuable
building-blocks for the design of electro- and photoactive hybrids
for optoelectronic devices. However, it appears that studies on
covalent hybrids is still largely unexplored. In consequence,
bonding of CNDs to other active units such as porphyrins,
chromophores of choice in artificial photosynthetic systems,[21]
could represent an intriguing and fascinating development.
Moreover, porphyrins hold several advantages over other types
of electro- and photo-active building blocks. Their 18 π-electron
aromatic structure gives rise to high molar absorption
coefficients and to efficient energy and/or charge-transfer
abilities.[22,23] Additionally, the possibility to tailor their redox
potentials through peripheral functionalization represents
another benefit.[24]
CNDs are produced by a variety of synthetic methods. On one
hand, molecular precursors are employed in “ bottom-up ”
approaches. On the other hand, “top-down” approaches are
based on cutting larger carbon materials. In recent years, a
range of methodologies have been developed to realize high
quality CNDs via simple, low-cost, green, and efficient synthetic
methods.[25–27] Recently, we reported a simple bottom-up method
to produce highly fluorescent nitrogen-doped CNDs (NCNDs),
characterized by small size and high fluorescence quantum
yields, by using a microwave (MW) reactor.[28] Arginine (Arg) and
ethylenediamine (EDA) were used as carbon and nitrogen
sources, and the corresponding NCNDs show a variety of
oxygen and nitrogen functional groups, which impart an
enhanced solubility in water. In addition, the presence of amino
groups amenable to further functionalization, allows linking to
further functional groups and/or active molecules/ions through
standard chemistry procedures.[29]
Carbon nanodots (CNDs) appear as a promising new class of
carbon nanomaterials,[1–3] possessing a number of intriguing
physicochemical properties, while, in contrast to other
nanocarbons, they feature a high intrinsic photoluminescence.[4]
This latter property draws considerable attention in the area of
light harvesting and in energy conversion schemes.[5–9] CND
features such as water solubility, biocompatibility and low
cytotoxicity have been the basis for bio-applications,[10–12] while
significant efforts have been made to use their
photoluminescence in lighting applications.[6,13–15] Next to their
strong photoluminescence, CNDs undergo charge-transfer
reactions, which widens the range of applications towards light
and electrical energy conversion.[16,17] For instance, CNDs
photoluminescence can be quenched, through charge-transfer,
either by electron acceptors (4-nitrotoluene and 2,4-
dinitrotoluene) or donors (N,N-diethylaniline), since CNDs can
act as electron donors or acceptors in their excited state.[17]
Following the pioneering charge-transfer studies, CND-based
hybrids began to emerge. In this context, leading examples are
SWCNT/CND,[18] PBI/CND,[19] and graphene oxide/CND
Until now, a large variety of non-covalent and covalent systems
based on porphyrins and nanocarbons, such as fullerenes,
carbon nanotubes, or graphene, have been described.[30–33]
Pioneering photophysical properties, both in solution and in the
solid state, have laid the foundations for their use as active
components in photovoltaic devices.[34–38] A substantial impact
on the ground and excited state interactions between porphyrins
and fullerenes, carbon nanotubes, or graphene have been
documented in covalently linked systems.[39–43] In most cases,
however, the covalent functionalization involves multi-step
[a]
[b]
Ms. F. Arcudi, Dr. L. Đorđević and Prof. M. Prato
Department of Chemical and Pharmaceutical Sciences, INSTM UdR
Trieste, Via Licio Giorgieri 1, University of Trieste, Trieste 34127
(Italy)
E-mail: prato@units.it
Dr. V. Strauss, Dr. A. Cadranel, Prof. Dr. D. M. Guldi
Department of Chemistry and Pharmacy & Interdisciplinary Center
for Molecular Materials (ICMM), Friedrich-Alexander-Universität
Erlangen-Nürnberg, Egerlandstr. 3, 91058 Erlangen (Germany)
E-mail: dirk.guldi@fau.de
synthetic
processes.
Moreover,
the
aforementioned
nanocarbons are poorly soluble in organic and aqueous solvents,
which renders their large-scale synthesis and use rather difficult.
Contrary to other nanocarbons, the surface of CNDs is rich in
functional groups, which provides high intrinsic solubility and
sites for further functionalization at the same time. Therefore,
CNDs are ideal candidates for the covalent decoration with
photo- and electro-active building blocks towards CND-based
hybrid materials.
[c,d] Prof. M. Prato
Carbon Nanobiotechnology LaboratoryꢀCIC biomaGUNE, Paseo de
Miramón 182ꢀ20009 Donostia-San Sebastián (Spain)ꢀ
Basque Fdn Sci, Ikerbasque, Bilbao 48013 (Spain)
Supporting information for this article is available on the WWW
under http://dx.doi.org/10.1002/anie.xxxxxxxxx
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10.1002/anie.201704544
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aryl and inner NH porphyrin resonances are all present in the 1H
spectrum of the hybrid, along with signals expected for NCNDs.
Additional evidence for the TArP-CONH-NCND formation came
from Raman spectroscopy (Figure S4, Supporting Information).
Notably, the strong NCND fluorescence precludes the recording
of any meaningful Raman spectra. However, quenching of the
NCND-based fluorescence in TArP-CONH-NCND (vide infra)
enabled the following Raman characteristics: on one hand,
Raman signals at 812, 971, 1000, 1083, 1144, 1242, 1330, 1363,
and 1452 cm-1 are in sound agreement with those reported for
H2TPP,[45] which confirm the presence of the porphyrin in the
hybrid. On the other hand, Raman signals at 1335 and 1555 cm-
1 relate to the D- and G-modes of NCNDs, respectively (Figure
SX) as seen for other CNDs.[46] An overall D/G intensity ratio of
0.59 reflects the co-existence of sp3 and sp2 carbons at a rather
similar distribution. A zeta potential of +6.36 mV in H2O/THF (1:1
v/v) suggests for NCND the presence of protonated amine
functionalities. For TArP-CONH-NCND, the zeta potential drops
to +1.53 mV, a finding consistent with the formation of amide
bonds, which lowers the number of protonated sites. As far as
the size of TArP-CONH-NCNDs is concerned, a value of around
5 nm (Figure S5, Supporting Information) was derived upon
probing with atomic force microscopy (AFM), which is in sharp
contrast to 2.5 nm determined for NCNDs, missing TArPs.[28]
The steady-state absorption and fluorescence spectroscopic
measurements of the TArP-CONH-NCND hybrid, as well as
TArP-COOH and NCND references, are reported in Figures S6
and S7 (Supporting Information). The absorption spectrum of
TArP-COOH reveals the typical Soret-band absorption at 414
nm and Q-band absorptions at 518, 555, 581, 636 nm (Figure
S6, blue trace). On the other hand, NCNDs (Figure S6, green
trace) exhibit a rather broad maximum at 287 nm and a
featureless absorption trailing into the visible. In the case of the
TArP-CONH-NCND conjugate, the Soret- and Q-band
absorptions are broadened and significantly red-shifted in H2O to
444, and 523, 556, 597, 650 nm, respectively. In addition, the
NCND absorption is blue-shifted by 6 nm, when compared to
that of the NCND reference (Figure S6, red trace). From the
latter shift, we deduce the close proximity between porphyrin
Figure 1. Reference and hybrid materials used in this study. Tetrakis(4-
carboxyphenyl)porphyrin (TCPP) and representative structure of nitrogen-
doped CNDs (NCNDs) references on the top and covalently linked porphyrin-
NCND (TArP-CONH-NCND) nanoconjugate on the bottom.
Herein, we report the first detailed photophysical study of an
electron donor-acceptor covalent nanoconjugate utilizing our
previously reported NCNDs as electron acceptors,[28] and
porphyrins as electron donors (Figure 1). The intramolecular
interactions in the porphyrin-NCND covalent hybrid are
investigated by steady state and transient absorption
measurements, in order to shed light on the dynamics of charge-
transfer and related processes.
The porphyrin-NCND hybrid was prepared through covalent
coupling (carbodiimide condensation reaction) of the free amino
functional groups of NCNDs with a carboxyphenyl peripheral
moiety of the (5,10,15-tri(4-tert-butylphenyl)-20-(4-carboxy
phenyl)porphyrin, TArP-COOH) (Figure 1).[28,44] The hybrid
material, named TArP-CONH-NCND, is obtained as a purple
solid by washing with organic solvents, dialyzing against H2O (to
remove any unreacted products), and finally freeze-drying. The
TArP-CONH-NCND nanoconjugate is readily soluble in H2O and
in polar organic solvents (such as MeOH and EtOH), resulting in
solutions stable for at least several weeks (Figure S1,
Supporting Information). The starting porphyrin for the coupling,
TArP-COOH, is only partially soluble in aqueous media and
therefore
the
5,10,15,20-tetrakis(4-carboxyphenyl)
porphyrin (TCPP, Figure 1) was used as
reference.
a water-soluble
One way to monitor the TArP-CONH-NCND formation was
employing FT-IR spectroscopy. The spectrum of the nanohybrid
(Figure S2, Supporting Information) shows the typical signatures
of NCNDs.[28] Additionally, it is notable the evolution of features
at 820 cm-1 due to out-of-plane bending vibration of the pyrrolic
C-H groups as well as at 1642 and 1570 cm-1 due to the
characteristic stretching and bending modes of the carbonyl and
N-H groups, respectively, of the amide linkage. This latter
follows the disappearance of the 1695 cm-1 feature due to the
carboxylic acid of free TArP-COOH. The successful
functionalization of the NCNDs surface with porphyrins was
observed also by 1H-NMR spectroscopy (DMSO-d6, 500 MHz
Figures S3, Supporting Information). Remarkably, the β-pyrrolic,
Figure 2. Excitation / emission 3D map for TArP-CONH-NCNDs in phosphate
buffered H2O (pH = 7.2) at room temperature.
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10.1002/anie.201704544
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and CND and their mutual communication in the ground state.
Additionally, the excited state was investigated in the TArP-
CONH-NCNDs by selectively exciting the NCNDs and the
porphyrin constituents at 300 and 422 nm, respectively, and
comparing them with the NCND and TArP-COOH references
(after adjusting to the same optical density) (Figure S7,
Supporting Info). Upon excitation at 300 nm, a drastic quenching
of the NCND fluorescence at 360 nm and the evolution of an
additional fluorescent feature at ~450 nm was observed. A
complementary excitation spectrum taken at 300 nm confirms
that a transduction of singlet excited state energy is responsible
for the NCND fluorescence quenching (from quantum yield 0.17
of NCNDs alone to 0.09 of the hybrid). Likewise, when the
porphyrin is selectively excited in TArP-CONH-NCNDs at 422
nm a significant fluorescence decrease at 645 nm is observed.
Finally, the fluorescence peaks are red-shifted from 645 and 715
nm, in the TArP-COOH reference, to 651 and 721 nm, in the
TArP-CONH-NCND conjugate, confirming the electronic
interactions between porphyrins and NCNDs in the excited state.
In contrast to the results obtained in H2O, complementary
absorption and fluorescence assays in H2O/THF (1:1 v/v)
showed only subtle changes. The absorption spectrum of TArP-
CONH-NCNDs is only slightly broadened in the Soret band
range, while the NCND-centered absorption is, like in H2O, blue-
shifted by ~8 nm (Figure S9, Supporting Information). When
comparing the fluorescence spectrum of TArP-CONH-NCNDs,
upon excitation at either 290 or 550 nm, with that of either the
evolves in all cases (Figure S9, Supporting Information). Similar
to the H2O experiments, an additional shoulder at ~445 nm
appears upon 300 nm excitation of TArP-CONH-NCNDs. In
contrast, the porphyrin fluorescence in TArP-CONH-NCND is
quenched by 40%, but was not shifted with respect to the
reference experiments with TArP-COOH.
Spectroelectrochemical and pulse radiolytical investigations
were carried out to shed light onto the electron acceptor and
donor properties of TArP-CONH-NCNDs and the corresponding
spectroscopic signatures upon one-electron reduction and/or
oxidation. To begin with, electrochemical measurements were
performed, in order to shed light on the redox properties of the
hybrid material. The oxidation potential at +1.19 vs. SCE related
to the porphyrin moiety was taken in account for the
spectroelectrochemical measurements (Figure S10, Supporting
Information). Next, spectroelectrochemical oxidation of TCPP
was
performed
in
buffered
H2O
(the
reference
tetracarboxyphenylporprhyrin was used due to solubility
reasons) (Figure S11, Supporting Information) besides radiolytic
reduction of NCNDs in H2O (Figure S12, Supporting Information).
In terms of TCPP oxidation, the differential spectra reveal in the
400 to 800 nm range minima at 530, 570, and 650 nm and
maxima at 460 and 700 nm as fingerprint absorptions of the
one-electron oxidized form of TCPP. In terms of NCND
reduction, a broad positive absorption evolves, which covers
most of the 400 to 800 nm region, and, relates to the
characteristics of the one-electron reduced form of NCND.
TArP-COOH or NCND references,
a
significant quenching
Finally, the nature of the TArP-CONH-NCNDs and TCPP excited
Figure 3. Top left: Differential absorption 3D map obtained upon
femtosecond pump probe experiments (λex
= 450 nm) of
TArP-CONH-NCNDs in H2O/THF (1:1 v/v) at room temperature.
Top right: Time absorption profiles and corresponding fittings at
680 nm (black) and 525 nm (red). Bottom left: Differential
absorption spectrum obtained upon femtosecond pump probe
experiments (λex = 450 nm) of TArP-CONH-NCNDs with a time
delay of 2.0 ps in 1:1 H2O/THF at room temperature
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10.1002/anie.201704544
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state and the underlying dynamics were investigated in H2O/THF
(1:1 v/v) (Figure 3) and in H2O (pH = 7.2) (Figure S13,
Supporting Information). Upon excitation at 450 nm, transient
absorption measurements with TCPP reference (Figure S14,
Supporting Information) gave rise to minima at 532, 570, 606,
and 660 nm, which reflect the ground state depletion of the Q-
band absorptions. Notably, the entire visible range is
superimposed by a broad positive transient stemming from
excited state absorptions. Overall, the deactivation is best
described by four transient / four lifetimes (Figure 4, left). It is
first a higher lying, second singlet excited state, which decays
with 2.4 ps via internal conversion. Secondly, it is the first singlet
excited state as product of the internal conversion. Next, a short-
and a long-lived decay is derived with 84.9 ps and 4.3 ns,
respectively. Here, 84.9 ps reflects the decay of aggregated
TCPP to the ground state, while 4.3 ns relates to the intersystem
crossing of monomeric TCPP to form the triplet excited state
(Figure 3, left). It is important to note that microseconds is the
lifetime of the triplet excited state. The situation is rather different
in TArP-CONH-NCNDs. In Figure 3, the minima, which are
discernable at 527, 558, 598 and 653 nm, confirm the porphyrin
excitation. Remarkably, immediately following the conclusion of
the 450 nm photoexcitation, a transient absorption spectrum is
discernable, which is in sound agreement with the sum of the
one-electron oxidized form of TCPP and the one-electron
reduced form of NCND. As such, charge separation seems to
evolve from a higher lying, second singlet excited state and, in
turn, to dominate even over the internal conversion (Figure 4,
right). Charge recombination is biphasic with 6.3 and 225 ps in
H2O as well as 10.0 and 246 ps in H2O/THF (1:1 v/v).
Importantly, in contrast to the TCPP reference, no evidence for
any internal conversion / intersystem crossing was established
(Figure 3, right).
than the first singlet excited state. Favorable thermodynamics
and strong mutual interactions are the driving forces for the
ultrafast charge separation. Excitation in the ultraviolet triggers a
cascade of energy transfers and charge separations.
Acknowledgements
The research leading to these results has received funding from
the University of Trieste, INSTM, the Seventh Framework
Programme [FP7/2007- 2013] under grant agreement n° 310651
(SACS project). Further financial support from MIUR (PRIN
contract No. 2010N3T9M4, FIRB RBAP11C58Y, FIRB RBAP11-
ETKA) is gratefully acknowledged. AC is a member of ALN and
acknowledges a DAAD-ALEARG postdoctoral fellowship.
Keywords: nanotechnology • carbon nanodots • porphyrins •
donor-acceptor • charge-separation
[1]
[2]
[3]
[4]
[5]
[6]
[7]
[8]
[9]
X. Xu, R. Ray, Y. Gu, H.J. Ploehn, L. Gearheart, K. Raker, W. A.
Scrivens, J. Am. Chem. Soc. 2004, 126, 12736–12737.
V. Georgakilas, J. a. Perman, J. Tucek, R. Zboril, Chem. Rev. 2015,
115, 4744–4822.
A. Cayuela, M. L. Soriano, C. Carrillo-Carrión, M. Valcárcel, Chem.
Commun. 2016, 52, 1311–1326.
S. N. Baker, G. A. Baker, Angew. Chem. Int. Ed. 2010, 49, 6726–
6744.
W. Kwon, G. Lee, S. Do, T. Joo, S. W. Rhee, Small 2014, 10, 506–
513.
X. Li, M. Rui, J. Song, Z. Shen, H. Zeng, Adv. Funct. Mater. 2015,
25, 4929–4947.
B. C. M. Martindale, G. A. M. Hutton, C. A. Caputo, E. Reisner, J.
Am. Chem. Soc. 2015, 137, 6018–6025.
B. C. M. Martindale, E. Joliat, C. Bachmann, R. Alberto, E. Reisner,
Angew. Chem. Int. Ed. 2016, 55, 9402–9406.
J. T. Margraf, F. Lodermeyer, V. Strauss, P. Haines, J. Walter, W.
Peukert, R. D. Costa, T. Clark, D. M. Guldi, Nanoscale Horiz. 2016,
1, 220–226.
In conclusion, we have reported a new study on an electron
donor-acceptor nanoconjugate, in which the light harvesting and
electron donating properties of meso-tetraarylporphyrins are, for
the first time, combined with the electron accepting features of
NCNDs. In addition to detailed photophysical studies, the hybrid
materials was extensively conjugated both with conventional and
uncommon techniques for carbon nanomaterials. Visible light
excitation transforms the strongly quenched porphyrin singlet
excited states in the TArP-CONH-NCND conjugate into charge
separated states. It is, however, a higher laying, second singlet
excited state, from which the charge separation occurs rather
[10]
[11]
[12]
[13]
L. Cao, X. Wang, M. J. Meziani, F. Lu, H. Wang, P. G. Luo, Y. Lin, B.
a Harruff, L. M. Veca, D. Murray, et al., J. Am. Chem. Soc. 2007,
129, 11318–11319.
P. G. Luo, S. Sahu, S.-T. Yang, S. K. Sonkar, J. Wang, H. Wang, G.
E. LeCroy, L. Cao, Y.-P. Sun, J. Mater. Chem. B 2013, 1, 2116–
2127.
S.-T. Yang, L. Cao, P. G. Luo, F. Lu, X. Wang, H. Wang, M. J.
Meziani, Y. Liu, G. Qi, Y.-P. Sun, J. Am. Chem. Soc. 2009, 131,
11308–11309.
X. Zhang, Y. Zhang, Y. Wang, S. Kalytchuk, S. V Kershaw, Y. Wang,
P. Wang, T. Zhang, Y. Zhao, H. Zhang, et al., ACS Nano 2013, 7,
11234–11241.
X. Guo, C.-F. Wang, Z.-Y. Yu, L. Chen, S. Chen, Chem. Commun.
2012, 48, 2692–2694.
G. A. M. Hutton, B. C. M. Martindale, E. Reisner, Chem. Soc. Rev.
2017, DOI 10.1039/C7CS00235A.
V. Strauss, J. T. Margraf, C. Dolle, B. Butz, T. J. Nacken, J. Walter,
W. Bauer, W. Peukert, E. Spiecker, T. Clark, et al., J. Am. Chem.
Soc. 2014, 136, 17308–17316.
[14]
[15]
[16]
[17]
[18]
[19]
X. Wang, L. Cao, F. Lu, M. J. Meziani, H. Li, G. Qi, B. Zhou, B. a
Harruff, F. Kermarrec, Y.-P. Sun, Chem. Commun. 2009, 3774–6.
V. Strauss, J. T. Margraf, T. Clark, D. M. Guldi, Chem. Sci. 2015, 6,
6878–6885.
V. Strauss, J. T. Margraf, K. Dirian, Z. Syrgiannis, M. Prato, C.
Wessendorf, A. Hirsch, T. Clark, D. M. Guldi, Angew. Chem. Int. Ed.
2015, 54, 8292–7.
[20]
P. Yu, X. Wen, Y.-R. Toh, Y.-C. Lee, K.-Y. Huang, S. Huang, S.
Shrestha, G. Conibeer, J. Tang, J. Mater. Chem. C 2014, 2, 2894–
2901.
[21]
[22]
K. Kalyanasundaram, M. Graetzel, Curr. Opin. Biotechnol. 2010, 21,
298–310.
J. Yang, M.-C. Yoon, H. Yoo, P. Kim, D. Kim, Chem. Soc. Rev.
2012, 41, 4808–4826.
[23]
[24]
L.-L. Li, E. W.-G. Diau, Chem. Soc. Rev. 2013, 42, 291–304.
G. de la Torre, G. Bottari, M. Sekita, A. Hausmann, D. M. Guldi, T.
Figure 3. Energy diagram for TCPP (left) and TArP-COONH-NCNDs (right)
This article is protected by copyright. All rights reserved.

10.1002/anie.201704544
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COMMUNICATION
Torres, Chem. Soc. Rev. 2013, 42, 8049–8105.
Y. Park, J. Yoo, B. Lim, W. Kwon, S.-W. Rhee, J. Mater. Chem. A
D. A. Vlad, C. Kusko, C. A. Dutu, A. Minoia, G. Deshayes, et al.,
Adv. Funct. Mater. 2012, 22, 3209–3222.
[25]
2016, 4, 11582–11603.
[39]
[40]
H. Imahori, Org. Biomol. Chem. 2004, 2, 1425–1433.
N. Karousis, A. S. D. Sandanayaka, T. Hasobe, S. P.
Economopoulos, E. Sarantopoulou, N. Tagmatarchis, J. Mater.
Chem. 2011, 21, 109–117.
[26]
[27]
S. Y. Lim, W. Shen, Z. Gao, Chem. Soc. Rev. 2015, 44, 362–381.
F. Arcudi, L. Đorđević, M. Prato, Angew. Chem. Int. Ed. 2017, 56,
4170–4173.
[28]
[29]
[30]
[31]
[32]
F. Arcudi, L. Đorđević, M. Prato, Angew. Chem. Int. Ed. 2016, 55,
2107–2112.
S. Carrara, F. Arcudi, M. Prato, L. De Cola, Angew. Chem. Int. Ed.
2017, 56, 4757–4761.
D. M. Guldi, G. M. A. Rahman, F. Zerbetto, M. Prato, Acc. Chem.
Res. 2005, 38, 871–878.
D. M. Guldi, G. M. A. Rahman, N. Jux, N. Tagmatarchis, M. Prato,
Angew. Chem. Int. Ed. 2004, 43, 5526–5530.
G. Bottari, O. Trukhina, M. Ince, T. Torres, Coord. Chem. Rev. 2012,
256, 2453–2477.
F. D’Souza, O. Ito, Chem. Soc. Rev. 2012, 41, 86.
T. Umeyama, H. Imahori, J. Phys. Chem. C 2013, 117, 3195–3209.
D. M. Guldi, Chem. Soc. Rev. 2002, 31, 22–36.
V. Sgobba, G. Giancane, S. Conoci, S. Casilli, G. Ricciardi, D. M.
Guldi, M. Prato, L. Valli, J. Am. Chem. Soc. 2007, 129, 3148–3156.
D. M. Guldi, G. M. A. Rahman, M. Prato, N. Jux, S. Qin, W. Ford,
Angew. Chem. Int. Ed. 2005, 44, 2015–2018.
[41]
G. M. A. Rahman, A. Troeger, V. Sgobba, D. M. Guldi, N. Jux, D.
Balbino, M. N. Tchoul, W. T. Ford, A. Mateo-Alonso, M. Prato,
Chem. - A Eur. J. 2008, 14, 8837–8846.
S. Campidelli, C. Sooambar, E. Lozano Diz, C. Ehli, D. M. Guldi, M.
Prato, J. Am. Chem. Soc. 2006, 128, 12544–12552.
D. M. Guldi, C. Luo, M. Prato, A. Troisi, F. Zerbetto, M. Scheloske,
E. Dietel, W. Bauer, A. Hirsh, J. Am. Chem. Soc. 2001, 123, 9166–
9167.
F. Wessendorf, J.-F. Gnichwitz, G. H. Sarova, K. Hager, U.
Hartnagel, D. M. Guldi, A. Hirsch, J. Am. Chem. Soc. 2007, 129,
16057–16071.
M. Aydin, D. L. Akins, in Appl. Mol. Spectrosc. to Curr. Res. Chem.
Biol. Sci. (Ed.: Dr. Mark Stauffer), InTech, 2016.
[42]
[43]
[44]
[33]
[34]
[35]
[36]
[45]
[46]
D. Li, D. Han, S.-N. Qu, L. Liu, P.-T. Jing, D. Zhou, W.-Y. Ji, X.-Y.
Wang, T.-F. Zhang, D.-Z. Shen, Light Sci Appl. 2016, 5, e16120.
[37]
[38]
C. Aurisicchio, R. Marega, V. Corvaglia, J. Mohanraj, R. Delamare,
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10.1002/anie.201704544
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Francesca Arcudi, Volker Strauss, Luka
Đorđević, Alejandro Cadranel, Dirk M.
Guldi* and Maurizio Prato*
Page No. – Page No.
Porphyrin Antennas on Carbon
Nanodots: Excited State Energy and
Electron Transduction
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