Corrole-BODIPY conjugates: Enhancing the fluorescence and phosphorescence of the corrole complex via efficient through bond energy transfer

Article abstract of DOI:10.1039/c5ra07250f

New corrole-BODIPY conjugates have been synthesized in high yield under mild conditions. Upon excitation at the absorption maximum of the BODIPY antenna chromophore, the fluorescence intensity of the free base corrole-BODIPY conjugate increases by ca. 300

Full text of DOI:10.1039/c5ra07250f

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ARTICLE
Corrole-BODIPY Conjugates: Enhancing the Fluorescence and
Phosphorescence of the Corrole Complex via Efficient Through
Bond Energy Transfer
Received 00th January 20xx,
Accepted 00th January 20xx
Wei Chen,a Jianfeng Zhang,b John Mack,c,* Gugu Kubheka,c Tebello Nyokongc and Zhen Shena,*
DOI: 10.1039/x0xx00000x
New corrole-BODIPY conjugates have been synthesized in high yield under mild conditions. Upon excitation at the
absorption maximum of the BODIPY antenna chromophore, the fluorescence intensity of the free base corrole-BODIPY
conjugate increases by ca. 300%, and significant phosphorescence intensity is observed for the iridium(III) complex of the
conjugate, while almost no phosphorescence is observed for the parent iridium(III) corrole, due to through-bond energy
transfer from the BODIPY antenna-chromophore to the corrole core.
www.rsc.org/
Cl
O
B
OH
K2CO3
Introduction
N
N
DCM rt
90%
N
N
B
F
F
F
F
2
1
There is considerable interest in the design of dye-sensitized
and organic photovoltaic cells. One of the most popular
approaches is to synthesize core-shell systems, which are
F
B
N
F
N
O
OH
comprised of antenna chromophores linked to
chromophore. Ideal candidates for this should absorb strongly
in 500 800 nm region with the antenna chromophores
transferring excitons to the central chromophore.1 Recently,
porphyrin-BODIPY (BODIPY boron dipyrromethene)
a core
Cl
B
F
F
F
F
F
F
F
F
F
F
F
F
F
F
F
NH
N
NH
N
NEt3
DCM rt
90%
−
F
F
F
F
N
N
NH HN
NH HN
F
F
F
=
3
4
conjugates have gained considerable attention, due to
favourable photophysical properties, such as very high
fluorescence quantum yields, and their other potential
applications, such as their use as fluorescent probes.2
Porphyrin derivatives have intense absorption bands in the
UV-visible region with high molar absorption coefficients, with
the exception of the blue-green region of solar spectrum
OH
F
F
HO
F
F
N
N
N
F
F
F
F
F
[Ir(cod)Cl]2
NH
N
Ir
N
N
F
F
THF reflux
pyridine
N
F
NH HN
F
F
F
F
F
F
F
F
5
F
550 nm).3
Since BODIPYs usually have intense
F
B
(450
−
N
N
absorption bands in the blue-green region,4 as well as other
desirable photochemical and photophysical properties, the
two chromophores can be viewed as being complementary in
terms of the solar spectrum, making their conjugates suitable
for solar cell applications.
F
F
Cl
B
O
F
NEt3
DCM rt
90%
F
N
N
N
N
N
F
F
F
Ir
N
N
N
F
F
F
F
Corroles are porphyrin derivatives that contain a direct
pyrrole-pyrrole bond and have broadly similar chemical
properties, but are better suited to stabilizing the higher
F
6
Scheme 1 Synthetic procedures for corrole-BODIPY conjugates 4 and 6.
oxidation states of a central metal ion, since the ligand
system is trianionic. To the best of our knowledge, there has
only been one example of corrole-BODIPY conjugate
π-
a
reported previously.5 Herein, we report a facile and high-yield
synthesis of a corrole-BODIPY conjugate and its iridium(III)
complex, Scheme 1, in order to study the impact of the BODIPY
antenna chromophore on the properties of the core corrole π-
system. The meso-halogenated BODIPY was synthesized
1
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according to literature procedures,6 and corrole
3 was
Table 1 Absorption and luminescence data (nm) for 2ꢀ6 measured at room
temperature in aerated and degassed toluene solutions for fluorescence and
phosphorescence, respectively, and fluorescence (ΦF) and phosphorescence
(ΦPh) state lifetimes (τair) and quantum yield values obtained upon excitation
at 416 and 460 nm and standardized against tetraphenylporphyrin (ΦF = 0.13
in toluene solution at 298 K).18
synthesized using the general method for A2B corroles.7
1
reacts readily with phenol under mild conditions to form
high yield. In a similar manner, corrole
complex , which contain a phenol moiety at the meso-
position, also readily react with the meso-halogenated BODIPY
to form and respectively, in high yield. Full
2
in
3
and its iridium
5
λabs
λem ΦF
ΦF
τair
/
ΦPh
ΦPh
τair
/
1
4
6,
416 nm
460 nm
416 nm
460 nm
characterization data are provided in the ESI.
(log ε)
ns
ꢁs
2
3
4
461(4.73) 502
416 (4.78) 662
ꢀꢀꢀ
96%
6.45 ---
4.44 ---
3.57 ---
---
---
---
---
---
---
Results and Discussion
11.3% 6%
11.6% 18%
415 (4.78) 658
460 (4.73)
5
6
416 (4.26) 662, 0.77% ---
830
8.47 0.32% ---
1.86
415 (4.23) 657, 0.77% 1.11% 4.22 0.36% 0.52% 1.78
460 (4.15) 830
Fig. 1 Normalized absorption spectra of 2 (black), 3 (blue) and 4 (red) in toluene
at room temperature.
The normalized UV-visible absorption spectra of 2-4 are shown
in Figure 1. The absorption spectrum of corrole-BODIPY
conjugate
460 (log ε = 4.73) nm, and is almost identical to the sum of the
spectra of corrole and BODIPY in this regard, Table 1.
4 has two intense bands at 415 (log ε = 4.78) and
3
2
These observations clearly demonstrate that there is no
significant ground-state interaction between the two
chromophores.8 Peaks associated with the BODIPY and corrole
moieties of 4 can also be readily identified by magnetic circular
dichroism (MCD) spectroscopy (Figure 2), since the absence
and presence of a cyclic perimeter results in very weak and
very intense MCD signals, respectively.
The optical spectroscopy of corroles can be described in terms
of perturbations to an ML = 0, ±1, ±2, ±3, ±4, ±5, ±6, ±7
3−
sequence of MOs associated with the parent C15H15
Fig. 2 Absorption and MCD spectra of
TD-DFT calculation calculated for the B3LYP geometry of
CAM-B3LYP functional with 6-31G(d) basis sets, is plotted against
secondary axis. Large red and blue diamonds are used to denote π→π
bands associated with the corrole and BODIPY moieties, respectively.
Green diamonds denote bands with charge transfer character between
different π-system moieties. The sign sequence of the Faraday B0 terms
4
in toluene at room temperature. A
perimeter for the 15 atom 18 π-electron system of the inner
ligand perimeter.9 Michl10 demonstrated that when the
symmetry of aromatic and heteroaromatic π-systems are
lowered by perturbations to the structure, the alignments of
4
by using the
a
*
the nodal patterns of the four frontier π-MOs of the parent
perimeter are retained. The HOMO and LUMO of the parent
3−
C15H15 perimeter for corroles have ML = ±4 and ±5 nodal
associated with the Q and B bands of the corrole π-system is highlighted
using the conventions of Piepho and Schatz.18 The details of the TD-DFT
calculation are provided in Table S1 in ESI. The fluorescence emission band
of
2 is plotted against an arbitrary axis to demonstrate the lack of
properties, respectively. By analogy with Gouterman’s 4-
orbital model11 it can be demonstrated that this leads to
allowed B (or Soret) and forbidden Q bands based on allowed
significant overlap with relatively narrow electronic absorption bands
associated with the S1 and S2 states, which cam be readily identified by
comparison with the MCD spectrum.
ꢀ
ML = ±1 and forbidden
introduced an -a and -s nomenclature for MOs whether
there is a nodal plane ( and -a) or antinodes ( and -s) aligned
ꢀML = ±9 transitions. Michl
a, s,
bands of
4 at 611, 563 and 410 nm, while there is a near
a
s
complete absence of MCD intensity at 456 nm, so the band
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can hence be readily assigned to the main BODIPY absorption
band (Figure 2). The results of a TD-DFT calculation carried out
on a B3LYP optimized geometry of
4 using the CAM-B3LYP
functional with 6-31G(d) basis sets are consistent with this
assignment (Table S1 in ESI). The MCD spectra of free base
with the y-axis of the corrole π
-system (Figure 3).10
Fig. 4 (a) Emission spectra of 4 (solid line) and 3 (dashed line) in aerated
toluene at room temperature. The blue lines are fluorescence spectra
measured upon excitation at 416 nm, while the red lines are for excitation
at 460 nm. The solutions of
the same optical density at 416 nm. (b) Fluorescence spectra of
upon excitation at 460 nm in toluene at room temperature. The solutions
of
(1.21 x 10−6 M−1) and (1.23 x 10−6 M−1) have the same optical density
at 460 nm.
3
(1.23 x 10−6 M−1) and
4
(1.23 x 10−6 M−1) have
and
2
4
2
4
Intense coupled pairs of Faraday B0 are observed for the Q and
B triarylcorroles exhibit an +/−/+/− sign sequence in the Q and
B bands in ascending energy terms (Figure S7).9a,12 This can be
readily explained by the significant lifting of the degeneracy of
the LUMO of the porphyrin
removed (Figure 3). Michl has demonstrated that a
sequence is observed when the splitting of the MOs derived
from the 1eg* porphyrin LUMO (referred to as the LUMO
π-system when a meso-carbon is
+/−/+/−
ꢀ
value, for the energy gap between the -a and -s MOs) is
greater than that of the MOs derived from the occupied 1a1u
and 1a2u frontier
as the HOMO value for the energy gap between the
MOs).10
π
-MOs of the porphyrin
π
-system (referred to
ꢀ
a
and s
Fig. 3 Angular nodal patterns for the frontier MOs of 1, 5 and 6 at an
isosurface of 0.02 a.u. (TOP). MO energies of 1-6 in TD-DFT calculations for
B3LYP geometries carried out using 6-31G(d) basis sets for 1-4 and SDD
Toluene solutions of
band of the corrole
3
and 4 were excited at 416 nm (in the B
-system) and 460 nm (the absorption
π
basis sets for
5
and
6
. Occupied MOs are denoted with small black square.
-MOs associated with Michl’s perimeter model10 for a
C15H15 − parent hydrocarbon perimeter are highlighted in light gray and are
labeled using Michl’s -a and -s MOs nomenclature. The 5d orbitals
associated with the Ir(III) ions of and are offset to the right. Dotted
lines are used to highlight trends in the energies of the HOMO and LUMO
of the BODIPY -system.
maximum of the BODIPY chromophore), respectively, to study
the energy transfer between the antenna chromophore and
the corrole ligand (Figure 4). Upon excitation at 416 nm, the
The four frontier
π
3
a, s,
5
6
emission spectra of both
3 and 4 contains one band at ca. 662
nm, in the region where fluorescence is typically observed for
π
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corroles. It should be noted, that
4
has almost the same If the energy is transferred primarily through the chemical
fluorescence intensity as
3,
but there is a slight bonds rather than through space, it depends on a mechanism
hypsochromatic shift, Table 1, due to the different meso- which is known as through-bond energy transfer (TBET).
substituent. In contrast, upon excitation at 460 nm, two Although there is no direct conjugation between the meso-
emission bands are observed for conjugate
at ca. 500 nm is associated with the emission from the BODIPY there is scope for the lone pair orbitals of the linking oxygen
antenna complex, while the emission band for the corrole atoms to interact with the two -systems. For example, the
4. A band centered phenyl substituent of the porphyrin and BODIPY moieties,
π
chromophore lies at ca. 662 nm. The fluorescence intensity recent spectroscopic characterization and theoretical analysis
from the S1 state of the corrole is stronger than that obtained of a novel nickel 10-oxacorrole complex by Kobayashi and co-
by direct excitation of the corrole core
These observations indicate that part of the energy absorbed form part of a cyclic
π
-system at 416 nm. workers demonstrated that an sp3 hybridized oxygen atom can
π
-system with properties very similar to
those of a conventional 18- -electron heteraromatic -system
of a porphyrinoid ligand.13 Using the commonly used formula
(fluorescence intensity of the
3 contains no significant corrole donor in the conjugate)/(fluorescence intensity of the free
by the BODIPY donor moiety is transferred to the corrole
system.
π
-
π
π
Upon excitation at 460 nm the fluorescence spectrum for an for energy transfer: 100×[1
−
equimolar mixture of and
2
emission band at 662 nm (Fig. S8, ESI). Evidence for significant donor)]%,15 the energy transfer efficiency for the TBET process
excited state energy-transfer is only observed when a BODIPY is estimated to be ca. 99%. Otsuki et al have demonstrated
antenna moiety is linked to a corrole core through a covalent that effective TBET can be mediated even when the bond is
aryl C
fluorescence quantum yield (Table 1), which makes the nm, the fluorescence intensity of
conjugate potentially suitable for use in solar cells. magnitude weaker than that of BODIPY
−
O bond. This results in a three-fold enhancement of the noncovalent.14 It is noteworthy that upon excitation at 460
at 502 nm is two orders of
, Figure 4. This is
4
A
2
significant contribution from Förster resonance energy what would normally be anticipated, however, since
transfer (FRET) is not likely in this context, since there is very deactivation of the S1 state is also likely to occur via
limited overlap between the emission band of BODIPY
nm and the main electronic band associated with the S1 state
in the Q band region of the spectrum of conjugate (Fig. 2).
2
at 502 nonradiative decay.16
4
Fig. 6 Normalized absorption spectra of 2 (black), 5 (blue) and 6 (red) in toluene
at ambient temperature.
Iridium porphyrins and their analogues have significantly
different photophysical properties from those of other
porphyrin complexes, since they phosphoresce in the NIR
region.17 The phosphorescent intensity is strongly dependent
on the nature of the axial ligand, and the highest
phosphorescence quantum yields are reported to be only ca.
1%,18 which makes them relatively unsuitable for use in
organic light-emitting diodes. The presence of a BODIPY
antenna chromophore can potentially enhance the intensity of
the NIR region luminescence. The Ir(III) corrole-BODIPY
Fig. 5 Absorption and MCD spectra of 6 in toluene at room temperature. A TD-
DFT calculation calculated for the B3LYP geometry of 6 by using the CAM-B3LYP
functional with SDD basis sets, is plotted against a secondary axis. Large orange,
red, and blue diamonds are used to denote metal-to-ligand charge transfer bands
and π→π* bands associated with the corrole and BODIPY moieties, respectively.
Green diamonds denote bands with charge transfer character between different
π-system moieties. The sign sequence of the Faraday B0 terms associated with
the Q and B bands of the corrole π-system is highlighted using the conventions of
Piepho and Schatz.20 The details of the TD-DFT calculation are provided in Table
S1 in ESI.
conjugate
absorption spectrum of
spectra of and
calculations of are broadly similar to those of
terms of the energies of the Q and B bands of the corrole
system and the main BODIPY absorption band, since the
energies of the frontier -MOs are largely unaffected by the
6
was found to emit beyond 800 nm (Table 1). The
is almost identical to the sum of the
The MCD spectroscopy and TD-DFT
(Figure 5) in
6
5
2.
6
4
π
-
π
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presence of the central diamagnetic Ir(III) ion (Figure 3). The the China-South Africa joint research program (CS08-L07) to ZS
presence of the 5dxz and 5dyz (dπ) orbitals close in energy to and JM and an NRF CSUR grant (93627) to JM. The theoretical
the a and s MOs of the corrole π-system enhances calculations were carried out at the Centre for High
configurational interaction between states associated with the Performance Computing in Cape Town.
porphyrin and BODIPY moieties (Table S1 in ESI), so there is
significant MCD intensity between the Q and B band regions
Notes and references
(Figure 5), in contrast with what is observed in the spectrum of
4
(Figure 3). In the NIR region (Figure 7), the phosphorescence
1
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emission intensity is clearly stronger upon excitation at the
2
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Fig. 7 Solid and dashed lines are used for the emission spectra of 6 and 5,
respectively, in toluene at room temperature, while black and red lines denote
excitation at 416 and 460 nm, respectively. The measurements were made on
solutions of 5 (1.35 × 10−6 M−1) and 6 (1.36 × 10−6 M−1) with the same optical
density at 416 nm.
6
7
(a)V. Leen, P. Yuan, L. Wang, N. Boens and W. Dehaen, Org. Lett.,
2012, 24, 6150.
absorption band maximum of the BODIPY antenna, due to
efficient energy transfer from the BODIPY antenna
chromophore to the iridium(III) corrole core. The slight
(a)D. T. Gryko and K. Jadach, J. Org. Chem.,2001, 66, 4267.(b) M.
J. Plater, S. Aiken and G. Bourhill, Tetrahedron, 2002, 58, 2405.
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6 compared to 5 (Table 1) is consistent
8
9
J. Y. Liu, E. A. Ermilov and D. K. P. Ng, Chem Comm., 2009, 1517.
with the presence of a nonradiative process associated with
the incorporation of a flexible antenna chromophore chain.19
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A corrole-BODIPY conjugate and its iridium(III) complex have
been prepared under mild conditions in high yield, so that the
luminescence enhancement in such core-shell systems can be
assessed. The efficient excited state energy transfer from the
11 M. Gouterman, In The Porphyrins; D. Dolphin, Ed.; Academic
Press: New York, 1978; Vol. III, Part A, pp 1-165.
BODIPY antenna chromophore to the core corrole π-system,
12 C. J. Ziegler, J. R. Sabin, G. R. Geier and V. N. Nemykin, Chem
Comm., 2012, 48, 4743.
results in an enhancement of the fluorescent intensity of the
corrole by 300%, while the phosphorescent intensity of the
iridium(III) corrole-BODIPY conjugate is also increased
markedly, making them potentially suitable for applications in
solar cells and OLEDs.
13 T. Ito T, Y. Hayashi, S. Shimizu, J.-Y. Shin, N. Kobayashi and H.
Shinokubo, Angew. Chem. Int. Ed., 2012, 51, 8542.
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Financial support was provided by the Major State Basic
Research Development Program of China (Grant Nos.
2013CB922101
& 2011CB808704), the National Natural
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Science Foundation of China (No. 21371090), the Natural
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