β-IminoBODIPY oligomers: Facilely accessible π-conjugated luminescent BODIPY arrays

Article abstract of DOI:10.1039/c7cc03279j

Imine-linked BODIPY oligomers show fluorescence quantum yields of up to 0.93. The azine linker may mediate π-conjugation that extends over six BODIPY units with redshifts up to 125 nm. BODIPYs are immobilized on silica gel through heterogeneous imine-bond

Full text of DOI:10.1039/c7cc03279j

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DOI: 10.1039/C7CC03279J
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‐IminoBODIPY oligomers: Facilely accessible π‐conjugated
luminescent BODIPY arrays
Received 00th January 20xx,
Accepted 00th January 20xx
Mizuho Tsuchiya,a Ryota Sakamoto,*ab Masaki Shimada,a Yoshinori Yamanoi,a Yohei Hattori,a
Kunihisa Sugimoto,c Eiji Nishiborid and Hiroshi Nishihara*a
DOI: 10.1039/x0xx00000x
www.rsc.org/
Imine‐linked BODIPY oligomers show fluorescenct quantum yields bonds are also known for the ability to mediate π‐
of up to 0.93. The azine linker may mediate π‐conjugation that conjugation.9 Despite such attracting properties as a linkage,
extends over six BODIPY units with redshifts up to 125 nm. imines are not commonly applied in π‐conjugated fluorescent
BODIPYs are immobilized on silica gel through heterogeneous dye molecules: rare cases have been reported by Skene.10 This
1
imine‐bond formation, being fluorescent and robust.
situation stems from imine’s tendency to quench the π‐π*
fluorescence of dye molecules; this is presumably due to its
low‐lying π* orbital, which can result in a photo‐induced
electron transfer (PET) quenching. Since the energy level of the
π* orbital of BODIPYs is lower compared to typical π‐
conjugated organic fluorophores, this quenching process is
expected to be less of an issue.
BODIPYs are one of the most important organic fluorophores.1
They feature favorable photophysical and photochemical
properties, such as intense absorption and fluorescence in the
visible region, whose fluorescence quantum yields (ϕF) often
reaching close to unity. Exploiting such favorable properties as
chromophores and fluorophores, BODIPYs have been
incorporated as fluorescent dyes,1 bioimaging probes,2 etc.
Although BODIPYs show excellent photofunctionalities as a
single unit alone, there are reports on systems with multiple
BODIPY units, extending their versatility as chromophores and
fluorophores.3‐6 Above all, π‐conjugated oligomeric species are
of great interest and importance because of their structural
rigidity and strong interactions among their individual
components, whose properties often lead to unique and
improved functionalities.
Imine bonds, or Schiff bases, formed by allowing amines
and aldehydes to react with each other, are well‐known
chemical bonds. The reaction proceeds under mild conditions,
such as room temperature, open‐air, and the optional
presence of an acid catalyst, whose only by‐product being
H2O.7 Molecular assemblies such as cages, macrocycles, etc,
have been developed using imine‐bond formation.8 Imine
a. Department of Chemistry, Graduate School of Science, The University of Tokyo, 7‐
3‐1, Hongo, Bunkyo‐ku, Tokyo 113‐0033, Japan.
b. JST‐PRESTO, 4‐1‐8, Honcho, Kawaguchi, Saitama 332‐0012, Japan
c. Japan Synchrotron Radiation Research Institute (JASRI), 1‐1‐1 Koto, Sayo‐cho,
Sayo‐gun, Hyogo, 679‐5198, Japan
d. Division of Physics, Faculty of Pure and Applied Sciences, Tsukuba Research Center
for Interdisciplinary Materials Science (TIMS) & Center for Integrated Research in
Fundamental Science and Engineering (CiRfSE), University of Tsukuba, 1‐1‐1
Tennodai, Tsukuba, Ibaraki, 305‐8571, Japan
†Electronic Supplementary Information (ESI) available: Experimental details;
crystallographic data; IR spectra; thermogravimetric analysis; fluorescence decay
curves; photophysical properties of the BODIPY‐loaded silica gel; cif files. See
DOI: 10.1039/x0xx00000x
Scheme 1 (a) Chemical structures of BODIPYs
synthesis of imine‐linked BODIPY dimers 6a2–6d2. (b) Synthesis of oligomers 7a
and isolated chemical species from the reactions mixtures, 7a3‐r and 7cn (n = 2–
6). (c) Immobilization of a formylated BODIPY ( or ) on amino‐terminated silica
gel (SG‐NH2) to obtain SG‐NH2‐3 and SG‐NH2‐4
1–4 and diamines 5a–d, and the
–c,
3
4
.
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S1, and S2, whereas those of 1, 2, and 3 are depicted in Fig. S3.
View Article Online
DOI: 10.1039/C7CC03279J
Their crystallographic data are summarized in Tables S1 and S2.
IR spectra of 1–3
TGA analysis results are shown in Fig. S5 and Table S3.
Photophysical properties of 1–3 6a2–6d2 7a3‐r and 7c2–7c6
, 6a2, 6c2, 6d2, and 7a3‐r are shown in Fig. S4.
,
,
in toluene solution are summarized in Table 1 and depicted in
Fig. 2, S6–S10. Also, their photographs are shown in Figure 3.
6a2 and 6b2 exhibit similar behavior: approximately 20 nm red‐
shifts of the absorption and fluorescence spectra from 2, with
nearly quantitative ϕF of 0.93. 6c2 and 6d2 with π‐conjugated
dimer structures displayed more distinctive spectral changes.
6c2’s absorption and fluorescence maxima are at 556 and 571
nm and 595 nm (ϕF = 0.50), respectively, which are red‐shifted
Fig. 1 ORTEP drawings of (a) 6a2; (b) 6c2∙2CH3OH; (c) 6d2; (d) 7c2. The thermal ellipsoids
are set at 50% probability. Color code: pink, boron; gray, carbon; purple, nitrogen; red,
oxygen; yellow green, fluorine. Hydrogen atoms and crystal solvent molecules are
omitted for clarity.
by approximately 70 nm from those of
2. Its absorption
spectrum is distorted, having a spectral shape of two
coalesced spectral bands. Thus, 6c2 exhibits substantial
spectral changes compared with 6a2 and 6b2. The major
difference should be attributed to the extended π‐conjugation
over the entire two BODIPY subunits in 6c2. Dimer 6d2 also
In this context, we synthesized a series of imine‐linked
BODIPY dimers (6a2‐6d2), by allowing 2‐formylBODIPY (2) and
diamines (5a‐d) to react with each other (Scheme 1a). The
concept of the dimers was further expanded to the
undergoes entirely different photophysics compared to
2,
whose absorption maximum is redshifted to 544 nm but
without detectable fluorescence. Oligomerization of BODIPY
units results in further modified spectroscopic properties. 7a3‐r
the ethylenediimine‐bridged trimeric ring, exhibited red‐
shifted spectra compared to 6a2, its analogous dimer. Its
absorption spectrum is bimodal, whose maxima are at 513 and
531 nm. Its fluorescence spectrum peaks at 564 and 609 nm
(ϕF = 0.78). The split absorption spectrum is ascribed to
through‐space exciton coupling between the BODIPY
subunits,11 which is reinforced by the immobilization of the
conformation among the BODIPY subunits upon the ring
structure formation. 7c2–7c6 experience absorption maximal
shift from 560 to 634 nm with the increase in the number of
the BODIPY subunit, while the fluorescence maxima shift from
604 to 644 nm. Therefore, 7c6 undergoes a redshift in
fluorescence by as many as 125 nm from referential monomer
corresponding oligomers, 7a(m)‐7c(m)
monofunctional with bifunctional 2,6‐diformylBODIPY (
(Scheme 1b). Purification of 7a(m) by size exclusion
chromatography allowed us to separate cyclic trimer 7a3‐r
while dimer to hexamer 7c2 7c6 were isolated from 7c(m)
(purification was unsuccessful for 7b(m)). The structural,
photochemical, electrochemical, theoretical, and
thermogravimetric properties of the dimers and oligomers
were disclosed. As another proposal of the utility of the imine‐
bond linkage, we demonstrated immobilization of formyl
,
by substituting
2
3)
,
,
–
BODIPYs
3 and 4 to silica gel through heterogeneous imine
chemistry (SG‐NH2‐3 and SG‐NH2‐4, Scheme 1c), which
realized robust tethering of the BODIPY dyes, retaining the
luminescent property.
Isolated dimers and oligomers 6a2–6d2, 7a3‐r and 7c2–7c6
were characterized by 1H and 13C NMR spectroscopy and high‐
resolution electrospray ionization mass spectrometry. ORTEP
3
emitting at 519 nm. This suggests gradual elongation of the
π‐conjugation from the dimer to hexamer, delocalizing over
drawings for 6a2, 6c2∙2CH3OH, 6d2, and 7c2 are shown in Fig. 1,
Fig. 2 Absorption and normalized fluorescence spectra of imine‐linked BODIPY oligomers and their precursors. (a,b) Absorption and normalized fluorescence
spectra of precursor and dimers 6a2 6d2. (c,d) Absorption and fluorescence spectra of cyclic trimer 7a3‐r. (e,f) Normalized absorption and normalized
and oligomers 7cn (n = 2–6).
2
–
fluorescence spectra of precursor
3
2 | J. Name., 2012, 00, 1‐3
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Table 1 Photophysical properties of BODIPY precursors
1
–
3
, dimers 6a2
–
6d2, cyclic trimer 7a3‐r, and oligomers 7cn (n = 2–6) in toluene
View Article Online
DOI: 10.1039/C7CC03279J
λabsa (nm)
504
502
absb (104 mol-1 L cm-1)
λfl (λex) c (nm)
F
e (ns)
kFf (108 s-1)
2.1
kNRg (108 s-1)
d
1
2
10.2
11.4
512 (484)
512 (492)
519 (491)
536 (480)
533 (480)
595 (550)
0.95
1.0
4.6
3.9
3.4
4.5
0.10
2.6
2.8
2.1
2.1
< 0.025h
0.11
3
510
527
521
556, 571
544
513, 531
560
612
625
12.2
12.2
12.9
9.78, 9.88
13.3
14.8, 14.0
12.4
0.96
0.93
0.93
0.50
6a2
6b2
6c2
6d2
7a3-r
7c2
7c3
7c4
7c5
7c6
0.16
0.16
4.5
1.7
2.9
2.9
i
i
i
i
i
-
-
-
-
-
564, 609 (513)
604 (540)
628 (612)
638 (615)
641 (620)
644 (620)
0.78
0.39
0.63
0.67
0.63
0.67
10.5
1.5
1.4
1.3
1.2
1.1
2.3
2.6
4.5
5.1
5.3
6.1
0.65
4.1
2.6
2.5
3.1
3.0
15.1
16
j
630
634
-
-
j
aabsorption maximum. bmolar absorptivity. cfluorescence maximum (λfl) and excitation wavelength (λex) dfluorescence quantum yield. efluorescence lifetime. fradiative decay
constant (ϕF / τ). gnon‐radiative decay constant ((1 ‐ ϕF) / τ). hprovidedϕF > 0.99. inot obtained due to weak signal. jnot obtained due to low solubility.
Fig. 3 Photographs of toluene solutions of BODIPY precursors 1–3, dimers 6a2–6d2,
cyclic trimer 7a3‐r, and oligomers 7cn (n = 2–6). Their appearance under ambient light
(top) and fluorescence upon illumination with 365 nm UV light (bottom).
the entire BODIPY subunits through the imine linkages. The
spectral shift gradually decreases, as the number of the
BODIPY subunits increases. This can be due to the exciton size
limit along the molecule and/or vibrational and/or rotational
distortions.12 However, since the red‐shift does not stop even
at 7c6, the effective π‐conjugation length of the oligomers
reaches at least 6.12,13 The ϕF value for 7c2 is somehow low
(0.39), but is improved substantially in 7c3–7c6, spanning 0.63–
0.67. The effect of the π‐conjugation was further studied by
electrochemistry (Fig. S11 and Table S4) and DFT calculation
(Fig. S12–S15 and Tables S5–S7).
Here we expand the imine‐BODIPY chemistry as a
convenient tool for immobilization of BODIPY dyes (Scheme
1c). BODIPYs
silica gel (SG‐NH2
3
and
4
14
were implanted on amino‐terminated
through heterogeneous imine‐bond
)
formation, to obtain SG‐NH2‐3 and SG‐NH2‐4, respectively (Fig.
4a–d). As reference samples, SG‐OH‐1 SG‐NH2‐1, and SG‐OH‐3
were also prepared: SG‐OH‐1 and SG‐OH‐3 stand for
unmodified silica gel with hydroxy residues (SG‐OH) to which
and are physisorbed. SG‐NH2‐1 comprises SG‐NH2 but should
miss imine‐bond immobilization because lacks a formyl
,
1
3
1
group. The load density of the samples is set at 1.0 × 10‐6 mol
g‐1. Fluorescence spectra and their parameters of the
decorated silica gel samples are shown in Fig. S16 and Table S8.
SG‐OH‐1, SG‐NH2‐1, and SG‐OH‐3 exhibit fluorescence maxima
at 506, 516, and 518 nm, respectively, similar to those of
corresponding BODIPYs in solution. On the contrary, SG‐NH2‐3
shows red‐shifted and broadened fluorescence spectra: indeed,
Fig. 4 Photographs of reactions of (a,b) 3 and (c,d) 4 with NH2‐terminated silica gel (SG‐
NH2) to form SG‐NH2‐3 and SG‐NH2‐4 before the reaction (left) and after 30 min (right)
SG‐OH‐3 and SG‐NH2‐3 possess different appearances and under (a,c) ambient light and (b,d) illumination with 365 nm UV light. (e) Photographs
of BODIPY‐loaded silica gel under ambient light and (top) 365 nm UV light irradiation
luminescence colors with one another (Fig. 4e). In SG‐NH2‐3
,
(bottom). (d‐h) Photographs of SG‐OH‐1, SG‐NH2‐1, SG‐OH‐3, and SG‐NH2‐3 in glass
tubes (f,g) before and (h,i) after a flush by methanol under (f,h) ambient light and (g,i)
illumination with 365 nm UV light. While SG‐NH2‐3 retains its fluorescence on silica gel
and shows minimal elution of the BODIPY dye, the rests released most of the dye
molecules. (j,k) Fluorescent microscopic images of (j) SG‐NH2‐3 and (k) SG‐NH2‐4 (top
the BODIPY molecule affords electronic perturbation by the
imine bond, to alter the appearance and luminescence color.
The imine‐bond formation is further supported by the fact that
the BODIPY dye in SG‐NH2‐3 does not elute off the silica gel left: with ambient light; top right: illumination with UV light (330–385 nm), detecting
fluorescence of λ > 420 nm; bottom left: illumination with blue light (460–495 nm),
detecting fluorescence of λ > 510 nm; bottom right: illumination with green light (530–
580 nm), detecting fluorescence of λ > 575 nm.)
upon methanol flushing, while SG‐OH‐1, SG‐NH2‐1, and SG‐
OH‐3 lose the majority of the BODIPY color and luminescence
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4
(a) A. Kamkaew, S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung
and K. Burgess, Chem. Soc. Rev., 2013D,O4I2: ,107.170;3V(9ibe/wC) 7ASCr.tiCcGl0eu3Oo2n7,li9nLJe.
Ma, J. Zhao, B. Küçüköz, A. Karatay, M. Hayvali, H. G.
(Fig. 4f–i). Fluorescence microscopic images were obtained for
SG‐NH2‐3 under illumination with UV (330–385 nm), blue
(460–495 nm), and green (530–580 nm) light (Fig. 4j). The silica
gel particles are faintly colored under ambient light, though
show intense fluorescence under illumination with the light
sources. Importantly, the luminescence images are completely
consistent with the silhouette of the silica gel particles,
demonstrating the BODIPY is successfully loaded onto the
silica gel. The fluorescence quantum yield of SG‐NH2‐3 is 0.64,
shown to retain the fluorescence ability upon chemisorption
on the silica gel. SG‐NH2‐4 features a color variation: exhibiting
red luminescence at 596 nm with a fluorescence quantum
yield of 0.50 (Fig. 4e, S16, Table S8). Fluorescence microscopic
images for SG‐NH2‐4 are shown in Fig. 4k, which feature bright
luminescence images well corresponding to the contours of
the silica gel microspheres.
In conclusion, imine‐linked BODIPY dimers and oligomers
were designed and synthesized. The azine and 1,4‐
phenylenediimine bridged oligomers exhibited photophysical
properties drastically different from the precursors, suggesting
that the electronic structures of the BODIPY cores were
modified through π‐conjugation. Of note, azine‐bridged
oligomers 7cn (n = 2–6) underwent redshifts in emission up to
125 nm as the number of the BODIPY subunits increased. The
imine‐bridged oligomers emitted with fluorescence quantum
yields of 0.39–0.93, retaining moderate to intense
luminescence upon the imine introduction. Heterogeneous
imine‐bond formation was applied in immobilizing BODIPY
dyes on a solid support: NH2‐passivated silica gel and
formylated BODIPYs were allowed to react, such that the
BODIPYs were bound promptly. The modified silica gel
fluoresced with quantum yields of 0.50–0.64, and
demonstrated much more robust retention of the BODIPY dyes
against methanol flushing than BODIPY dyes physisorbed on
silica gel. The present research has demonstrated the
versatility and compatibility of applying imine linkage to
BODIPYs, and broadened the chemistry of both imine and
BODIPY, contributing to the development of photofunctional
assemblies and materials.
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4 | J. Name., 2012, 00, 1‐3
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