Three colour solid-state luminescence from positional isomers of facilely modified thiophosphoranyl anthracenes

Article abstract of DOI:10.1039/d0cc02585b

Three positional isomers of thiophosphoranyl anthracene were synthesized and their photophysical properties were investigated. By varying the position of the substituents, blue, green and yellow solid-state fluorescence with differences in the emission wa

Full text of DOI:10.1039/d0cc02585b

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Three colour solid-state luminescence from positional isomers of
facilely to modify thiophosphoranyl anthracenes
Timo Schillmöller,a Paul Niklas Ruth,a Regine Herbst-Irmer a and Dietmar Stalke *a
Received 00th
January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Three positional isomers of a thiophosphoranyl anthracene were monomeric form of the fluorophore.1,10 More recently, efficient
synthesized and their photophysical properties investigated. By solid-state emitters have been reported, which reveal a dimeric
variation of the substiuents’ position, blue, green and yellow solid- motif with strong π-π interactions of polyaromatic fluorophores
state fluorescence with a difference in the emission wavelength of resulting in an intense excimer emission.11 This way large
over 100 nm could be established, which is assigned to intra- and bathochromic shifts of the emission wavelengths could be
intermolecular effects.
obtained. For the anthracene fluorophore, which usually emits
in the blue region and can be used for photon up-conversion via
triplet-triplet annihilation12, efficient solid-state fluorescence in
the green region with emission wavelengths up to 525 nm was
achieved.13-15 Generally, the anthracene scaffold is substituted
with a suitable group in the reactive 9-position and weak
interactions of the aromatic moieties result in a dimeric motif in
the solid-state, which is suitable for excimer emission.13-15 In
Weak intermolecular interactions play
a key role in
understanding the photophysical properties in luminescent
solid-state materials.1,2 The traditional view of Aggregation-
Caused-Quenching (ACQ), which ascribes the commonly
observed fluorescence quenching of highly solution-emissive
fluorophores in the solid state to strong intermolecular
interactions, has been overhauled.3 In the recent years many
concepts and strategies have been developed for tuning and
improving the solid-state emission of organic molecules, which
has been classically achieved by metal-based compounds.4 The
most famous concept is known as Aggregation-Induced-
Emission (AIE) and comprises compounds, which are non or only
barely luminescent in solution but emit upon aggregation.5,6
Typically, AIE-luminogens consist of a fluorophore substituted
with a group able to actively rotate or vibrate in solution,
causing an efficient quenching. When these compounds
aggregate the internal motion is restricted and an enhanced
solid-state emission is obtained.7 Tetraphenylethylene8 (TPE)
and hexaphenylsilole5,9 (HPS) are commonly used groups in AIE-
materials and a plethora of AIE-type fluorophores are already
investigated. Further approaches try to overcome ACQ by
introducing bulky substituents to the fluorophore or by co-
crystal formation yielding less interchromophoric interactions
and enhanced solid-state emission, which originates from the
this paper we present the positional isomers of
a
thiophosphoranyl anthracene. By substituting the uncommon
1- and 2-positions of anthracene solid-state emission in three
colours with differences in the emission wavelength of more
than 100 nm was observed. Surprisingly, a yellow excimer
emission from the 1-isomer was observed, which is quite a rare
colour for structurally simple anthracene derivatives.
Therefore, modifications in the 1-position of the anthracene
could be a promising strategy for obtaining longer wavelengths
emission in the solid-state.
a.Institut für Anorganische Chemie, Georg-August-Universität Göttingen,
Tammannstraße 4, 37077 Göttingen, Germany.
E-mail: dstalke@chemie.uni-goettingen.de
Electronic Supplementary Information (ESI) available:
See DOI: 10.1039/x0xx00000x
Fig. 1. Crystal structures of thiophosphoranyl anthracenes 1 (left), 2 (middle) and 3
(right) in the front view (top) and side view (bottom). For 3 the quantification of the
anthracene bending is shown by the folding angle α.
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1-3 reveal a structured
Herein, we report the synthesis and investigation of the The UV-VIS absorption spectra of
structure-property relationship of the two positional isomers of absorption band from 340 to 410 nm, wDhOicIh: 1i0s.1a0s3s9i/gDn0eCdC0to25t8h5Be
the previously investigated [9-(S)PPh2(C14H9)]16
). [2-(S)PPh2- S0 S1 transition mainly located on the anthracene core and
(C14H9)] ( ) was prepared from 2-bromoanthracene similar to polarized along the short anthracene axis (see Fig. 2). Therefore,
the reported procedure for the 9-substituted derivative by and show a slightly stronger red shift compared to as the
lithiation and subsequent addition of chlorodiphenylphos- substituent is located on the short molecular axes. For the
phane.17 Oxidation of the P(III) was achieved with elemental vibrionic structure is less pronounced due to the strong
sulfur in toluene. [1-(S)PPh2(C14H9)] ( ) was synthesized starting distortion of the anthracene plane. The emission spectra of
from 1-chloroanthracene by nucleophilic substitution with and in diluted solution are nearly identical and resemble also
lithium diphenylphosphanide and subsequent sulfur oxidation. the structure of the parent anthracene with a vibronic emission
Shifting the substituent from the 9-position to the outer from 390–460 nm. The emission maximum of is further red-
anthracene ring leads to a small downfield shift of the 31P-NMR shifted to 462 nm and the vibronic structure is completely lost,
resonance from about 35 ppm ( ) to 42-43 ppm (
), which is which is assigned to the bent structure of the anthracene.15d
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(
3
→
2
1
3
2
3
1
1
2
3
3
1,2
more typical for thiophosphoranyl substituted aromatic The emission in solution is generally weak due to a photo-
compounds.16d,18 Furthermore, the oxidation leads to an induced electron transfer from the sulfur lone pair to the
increased stability compared to the P(III) precursors, which can anthracene, which results in an efficient quenching (see Table
undergo a slow oxidation in air.
S4). The emission intensity enhances when the aggregation is
Single crystals of and for structure determination were forced by addition of different water fractions to the THF
1
2
obtained by recrystallization from toluene. Both compounds solution (see Figs. S13-S15). Furthermore, a slight red-shift and
crystallise in a monoclinic crystal system in the space groups a broadening of the spectra is observed at higher water
P21/c (1) and P21/n (2). The solid-state structure of 3 was fractions. When going to the solid-state the emission properties
reported earlier15 and reveals a triclinic crystal system in the change dramatically (see Fig. 3 and Table 1). For
2 the changes
̅
space group P
anticipated,
1
with two molecules in the asymmetric unit. As are only small and as in solution a blue emission can be
2
1
and
reveal nearly planar anthracene moieties in observed in the range from 420–510 nm. The structured
, with a emission is still present even less pronounced compared to the
folding angle α of 11.67(13) ° and 16.86(11) °, respectively (see diluted solution. For also a further red-shift of 20 nm
contrast to the strongly butterfly-bent structure of
3
3
Fig. 1, Figs. S1-S2 and Table 1). Locating the bulky substituent at compared to the solution emission is found, resulting in a blue-
the outer anthracene ring induces less steric strain and different green emission in the solid-state. The shape of the spectrum is
conformation of the substituent regarding the anthracene comparable with the structureless emission band in solution.
plane. While in
anthracene plane resulting in a S-P-C-C torsion angle ω of solid-state a yellow emission with a wavelength of 545 nm is
80.84(10)° and 89.01(10)° in and a decrease of ω ( obtained. Compared to the solution spectra the emission
64.06(14)°, : 4.3(3)°) together with a changed substituent wavelength reveals a bathochromic shift of over 100 nm.
orientation is observed. Due to the more flexible orientation in Furthermore, the vibronic structure is completely gone and a
and no bending of the anthracene is observed. Furthermore, largely broadened emission spectrum that ranges over 200 nm
the CAnth–P bond is slightly shortened and the CPh–P–CPh angle γ is obtained in the solid-state. Solid-state luminescence in the
3 both phenyl groups are located above the For 1 the emission changes drastically upon aggregation. In the
1
2
1:
2
1
2
is increased for
1
and
2
indicating a less strained structure.
yellow region is quite rare for small anthracene derivatives
without any conjugated substituent. As already mentioned, the
hitherto reported anthracene excimers showed emission in the
green with maximum wavelengths of about 525 nm. The three
positional isomers of the thiophosphoranyl anthracene reveal
three colour emission in the solid-state with a difference in the
emission wavelength of over 100 nm. The electronic structure
of all three should be comparable as the absorption and
Table 1. Structural and solid-state photophysical properties of the
thiophosphoranyl positional isomers 1 – 3.
1
2
3
CAnth–P / Å
γ / °
1.8135(17)
1.812(2)
1.8326(13)
1.8327(13)
101.65(6)
100.95(6)
80.84(10)
89.91(10)
11.67(13)
16.86(11)
21.1
104.62(8)
64.06(14)
1.4(2)
106.58(10)
4.3(3)
ω / °
α / °
3.50(19)
Overlap / %
dπ-π / Å
dx / Å
dy / Å
λem / nm
τ / ns
42.3
3.325
1.070
1.057
545
0
-
3.242
-
1.344
-
426 / 441 / 469 / 502
3.2 / 7.8
3.227
484
1.4 / 3.2
4.0
Fig. 2. (a) Normalized UV-Vis and (b) normalized emission spectra of positional isomers
1 - 3 in diluted THF solution (10-5 M, λex = 350 nm).
29.0
5.9
ΦF / %
15.7
2 | J. Name., 2012, 00, 1-3
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Fig. 3. (a) Normalized solid-state emission spectra of positional isomers and (b)
photographs of bulk samples of 1 – 3 under daylight (top) and under UV-light (bottom).
emission spectra in solution differ only slightly. Therefore, a
closer look into the solid-state structures of 1-3 is needed to
explain the large deviations of the emission spectra in the
aggregated state.
Fig. 5. (a) Crystal packing of [1-(S)PPh2(C14H9)] (1) revealing strong face-to-face and
end-to-face interactions of the anthracenes (bold). (b) Detailed view on the
observed dimeric motif with a decent overlap of the anthracene planes.
Isomer
2 reveals the smallest changes in the emission spectra
upon aggregation. Both, the solution and solid-state fluores-
cence resemble the emission of unsubstituted anthracene. The
solid-state structure is also closely related to pure anthracene.
No face-to-face interactions between the anthracene scaffolds
can be observed and closest interactions of two anthracene
cores are found in an end-to-face manner with C–H···π
distances of around 2.8 Å (see Fig. 4). Further interactions are
present between the phenyl groups of the backbone and
neighbouring anthracenes in similar C–H···π distances (see Fig.
S4). Through these general weak interactions towards the
chromophore the emission spectra are barely affected upon
3
. The unusual large bathochromic shift of
emission is assigned to strong intermolecular interactions. The
dimeric motif of is also dominant in the solid-state structure
of (see Fig. 5). The overlap is enlarged to about 42.3 % as the
offset dy along the long-molecular anthracene axes is decreased
by over 2 Å to 1.057 Å compared to . The π–π distance with
1 resulting in a yellow
3
1
3
3.325 Å is only slightly elongated. The shift of the substituent
from the central to the outer anthracene ring leads to a new
orientation of the substituent and therefore a less shielded
anthracene site, which allows a larger overlap with less offset of
two anthracenes and consequently stronger π-π interactions.
Therefore, the solid-state structure of
formation of an excimer. In comparison to
upon aggregation are much more pronounced. The emission
spectrum is extremely broadened, and the bathochromic shift
reaches nearly 100 nm. Together with the increased lifetime to
almost 30 ns an excimer formation as origin of the yellow
aggregation. For the isomer
3 with the substituent located in
1
seems suitable for the
the changes in
the 9-position at the central ring changes in the emission
spectra are already seen in solution. The loss of the vibronic
structure and the larger bathochromic shift was ascribed to the
strong folding and deformation of the anthracene plane. In the
solid-state a further bathochromic shift was found, which was
attributed to moderate face-to-face interactions between two
anthracenes resulting in a green emission. The mean π-π
distance of these anthracene dimers is about 3.242 Å and the
overlap was determined to only 21.1 %. As the broadened signal
is already observed in solution and the fluorescence’ lifetime is
only a few nanoseconds an excimer formation is not assumed,
and the emission is mainly attributed to the monomeric form of
3
1
fluorescence of
1 can be confirmed. Besides the dimeric motif
further end-to-face interactions between anthracenes are
observed, which lead to a ladder-type stacking with overall
strong intermolecular interactions (see Fig. 5 and Fig. S6). The
quantum yields increase in the solid-state as the quenching by
the sulfur lone pair is probably less effective due to the more
rigid structure. Future research will focus on introduction of
different substituents to increase emission efficiency and
potentially leading to stronger overlaps and even more shifted
emission wavelengths.
In conclusion, we have presented three positional isomers of a
thiophosphoranyl anthracene, which reveal solid-state
fluorescence in three different colours and differences in
emission wavelengths of over 100 nm. Analyses of the solid-
state structures and the photophysical properties could ascribe
the unusual yellow emission to the formation of an excimer in
the solid-state. Therefore, substitution in the 1-position of the
common anthracene fluorophore with suitable substituents
could be a promising strategy for obtaining long-wavelength
emission in the solid-state by structurally easy to modify
compounds.
Fig. 4. Crystal packing of [2-(S)PPh2(C14H9)] (2) showing a herringbone-type packing of
the anthracene moieties (bold). View along crystallographic a-axes (a) and along
crystallographic c-axes (b). Disorder is omitted for clarity.
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