A soluble conjugated porous organic polymer: efficient white light emission in solution, nanoparticles, gel and transparent thin film

Article abstract of DOI:10.1039/c6cc08903h

A tetraphenylcyclopentadiene based multifunctional, solution processable, fluorescent, ultramicroporous polymer exhibiting high hydrogen uptake was employed for encapsulation of dyes to obtain enhanced white light emission in solution, nanoparticles, gel and transparent thin film. Hybrid nanoparticles showed a quantum yield of 35% with a high color rendering index.

Full text of DOI:10.1039/c6cc08903h

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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
Reactivity differences of Sc
first methanofullerene derivatives of Sc
3
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Soluble conjugated porous organic polymer: efficient white light
emission in solution, nanoparticles, gel and transparent thin film
Received 00th January 20xx,
Accepted 00th January 20xx
‡
‡
Pragyan Pallavi, Sujoy Bandyopadhyay, Jesna Louis, Arundhati Deshmukh and Abhijit Patra*
DOI: 10.1039/x0xx00000x
www.rsc.org/
Tetraphenylcyclopentadiene based a multifunctional, solution
processable, fluorescent, ultramicroporous polymer exhibiting
high hydrogen uptake was employed for encapsulation of dyes to
obtain enhanced white light emission in solution, nanoparticles,
gel and transparent thin film. Hybrid nanoparticles showed a
quantum yield of 35% with high color rendering index.
White light emitting (WLE) materials have gained significant
attention because of its multi-stimuli responsive properties
1
-3
and applications in lighting and display devices.
The
extensive use of hazardous mercury vapour in commercial
white light emitting devices like fluorescent lamps possesses a
serious threat to the environment. Thus, the development of a
cost-effective, environmentally benign and convenient
protocol for solid state white light emission with high quantum
efficiency is in increasing demand. The WLE system can be
Fig. 1 The schematic illustration depicting the versatile use of a strongly fluorescent and
soluble porous organic polymer (TPDC-BZ) for hydrogen uptake and efficient white light
obtained with the combination of three primary colors blue, emission in solution, nanoparticles (NPs), gel and thin film, by utilizing energy transfer
green and red or only blue and yellow covering the wavelength between the polymer and encapsulated dyes.
4
,5
range of 400-800 nm. The typical WLE material is designed
using the combination of multichromophoric components or a
energy transfer between the polymer and encapsulated dyes
leading to the tuning of fluorescence including white light
6
,7
single molecular material with multifunctional emitters.
1
9
Various kinds of materials based on small organic molecules,
π-conjugated polymers and porous solids like metal-organic
frameworks (MOFs) have been explored for white light
emission. However, due to the lack of solution processability
of CPOPs, fabrication of white light emitting system with high
quantum yield still remain a challenge. As proposed by Cooper
and coworkers, processability has now been considered as an
1
-8
emission.
2
0
Currently, the conjugated porous organic polymers
CPOPs) have emerged as fascinating materials with diverse
important functional property of new porous materials. Thus,
imparting solution processability in CPOPs and utilizing them
for efficient white light generation is an important research
problem to address.
(
applications in gas storage, catalysis, light harvesting, energy
9
-18
storage and chemo/bio-sensing. In addition to high thermal
and hydrothermal stabilities due to the covalent bonds, the
unique combination of π-electron conjugation as well as
porosity makes CPOPs highly promising for multifunctional
We have synthesized a strongly fluorescent, soluble CPOP
using tetrakis-(4-bromophenyl)-5,5-dioctyl cyclopentadiene
(TBDC) and benzothiadiazole (BZ). The polymer (TPDC-BZ, Fig.
1
2
applications. The porous structures affect the efficiency of
1
) exhibited ultramicroporosity and an appreciable H uptake
2
capacity. This communication focusses on the fabrication of
efficient WLE systems in four different forms viz. solution,
aqueous dispersion of nanoparticles, gel as well as the
transparent thin film by incorporating suitable fluorescent
dyes in TPDC-BZ polymer matrix (Fig. 1). The excited state
processes were elucidated by time-resolved emission spectra
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measurements. Even though very few examples of fabrication
Journal Name
1
9,21
of WLE materials based on porous polymers exist,
to the
best of our knowledge, the present study is the first report on
implementation of solution processable CPOP for the efficient
generation of white light as many as four different forms.
Extensive crosslinking in the network polymers reduces
solubility. Hence, a simple, easily attainable fabrication
method resulting in soluble CPOP with high surface area is
desirable. In this study, we developed highly porous and
Fig. 2 (a) Nitrogen sorption isotherm of TPDC-BZ at 77 K; inset: pore size distribution
4 2
strongly fluorescent soluble CPOP by employing A + B type
estimated using NLDFT method (black squares: differential pore volume and blue
Suzuki-Miyaura polycondensation between TBDC and 2,1,3- squares: cumulative pore volume). (b) H2 sorption isotherm of TPDC-BZ at 77 K. Black
benzothiadiazole-4,7-bis(boronic acid pinacol ester) (Scheme circles: adsorption and red circles: desorption.
S5, see ESI†). The resultant polymer TPDC-BZ was found to be
soluble in common organic solvents like toluene, hydrogen sorption profile show type III adsorption isotherm.
3
-1
tetrahydrofuran
dichloromethane (DCM). The long alkyl chains in tetraphenyl)-
,5-dioctyl cyclopentadiene (TPDC) impart flexibility and help TPDC-BZ is higher than the reported soluble CPOP like SCMP1
(THF),
chloroform
(CHCl3)
and H uptake by TPDC-BZ was found to be 143 cm g (6.4 mmol
2
-1
g
or 1.3 wt% at 1 bar, 77 K, Fig. 2b). H uptake capacity of
2
5
-1
2
-1 20a
to solubilize the polymer. High surface area, solution (3.9 mmol g , S = 505 m g ) and comparable to insoluble
BET
processability and strong low-energy fluorescence open up the microporous polymers having similar surface areas under
2
possibilities of multifunctional applications using TPDC-BZ (vide identical conditions such as CPOP-7 (1.5 wt%, S = 1430 m g
-
BET
1
9d
2
-1 9f
infra).
), BB-POP-3 (1.1 wt%, S = 560 m g ), BDT-2 (1.5 wt%,
BET
2
-1 12
The FTIR spectrum of TPDC-BZ show the characteristic SBET = 571 m g ). The efficient hydrogen uptake by TPDC-BZ
-1
bands corresponding to aliphatic C-H stretching (2850 cm and is attributed to its small pore size. It has been observed that
-1
-1
925 cm ), C -H stretching (3046 cm ) and aromatic C=C small pores facilitate the interactions of hydrogen molecules
2
Ar
-1
1
24
stretching (1482 cm , Fig. S1 ). H NMR spectrum of TPDC-BZ with pore walls leading to higher enthalpies of adsorption.
compared with that of constituent monomers clearly indicates The electronic absorption spectrum of TPDC-BZ in THF
similar resonances in addition to other resonances shows peaks at 305 and 388 nm (Fig. S12 ). Absorption peaks
demonstrating polycondensation between the monomers (Fig. at UV region are presumably due to π–π* transition of the
). C NMR of TPDC-BZ shows the peaks at 153 and 155 conjugated framework. Absorption and excitation spectra
ppm attributed to benzothiadiazole moiety and the peaks at were found to be similar in solvents of varying polarity (Table
4 to 35 ppm correspond to the aliphatic carbons of TPDC core S1 ). TPDC-BZ polymer showed strong yellow fluorescence in
Fig. S5 ). The weight average molecular weight (Mw) of TPDC- THF (ꢀꢁ = 46%) with a peak at 577 nm (Fig. 1 and 3a). Emission
†
†
1
3
S4†
1
†
(
†
BZ was found to be 5.4 kDa with a polydispersity index of 1.5 spectra depict a considerable red shift as the solvent polarity
as determined by gel permeation chromatography (GPC, Fig. increases; emission maximum shifts from 550 nm in toluene to
S6). The thermogravimetric analysis (TGA) indicates that the 600 nm in DCM (Fig. 3a). Such positive solvatochromism in
ο
polymer is thermally stable up to 370 C (Fig. S7†
morphology of the TPDC-BZ as characterized by field emission originating from the benzothiadiazole moiety.
). The surface emission indicates a highly polar excited state, presumably
3
1
scanning electron microscopy (FESEM), reveal globular
morphology with rough surfaces (Fig. S8 ).
TPDC-BZ can provide a promising scaffold for encapsulating
dyes due to its porous nature. Therefore, a blue emitting dye
†
Nitrogen sorption profile of TPDC-BZ was found to follow 5-octyl-1,2,3,4,5-pentaphenyl-1,2-cyclopentadiene
(OPCP,
ꢃꢄꢅꢆꢆ
ꢂꢃ
type (II) adsorption isotherm (Fig. 2a). At low-pressure region, Scheme S6,
λ
ꢇ 435ꢆꢈꢉ
)
was mixed with yellow
-
1
high gas uptake indicates microporous nature of the polymer. fluorescent TPDC-BZ. 0.5 mg mL of TPDC-BZ and 0.1 M OPCP
The Brunauer-Emmett-Teller (BET) surface area of TPDC-BZ in THF were used as stock solution. The concentration of blue
2
-1
were estimated to be 610 m
g
(Fig. 2a, Fig. S9a). The and yellow emitting solution was optimized to get the white
). Three parameters to evaluate the
to be 330 m g and 280 m g respectively as determined by quality of white light are Commission Internationale de
t-plot method (Fig. S10). TPDC-BZ was obtained by rapid Eclairage (CIE) coordinates (x = 0.33, y = 0.33), color rendering
precipitation of chloroform solution to ultracold methanol. It index (CRI
has been observed by researchers that rapidly precipitated CIE color coordinates of x = 0.34, y = 0.31 were obtained for
polymers show high surface area because of the inefficient WLE solution (ꢀꢁ = 14%) containing 5 M of OPCP in 2.5 mL of
). The CRI value was found to be
). The CCT for WLE solution is 5290 K, which is
close to that of daylight and in the range of electronic
The pore volume of TPDC-BZ is 0.73 cm g at a relative flashlight. Lifetime measurements of WLE solution suggest that
pressure of P/P = 0.99. The pore size was found to be 0.7 nm there is no significant energy transfer (ET) between OPCP and
micropore surface area and external surface area were found light emission (Fig. S13
†
2
-1
2
-1
l′
1
,8
†
) and correlated color temperature (CCT†). The
ꢀ
2
2
packing. During the course of precipitation, the collapsing of TPDC-BZ solution (Fig. S13d
†
2
3
pores is restricted due to relatively smaller strut length, as is 84 (Fig. S13e
the case in TPDC-BZ leading to its higher surface area.
†
3
-1
0
as determined by nonlocal density functional theory (NLDFT) TPDC-BZ (Fig. S13f and Table S2
†).
method indicating ultramicroporous nature (Fig. 2a, inset). The
2
| J. Name., 2012, 00, 1-3
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Fig. 4 (a) Excitation spectra of nanoparticle dispersions monitored at different emission
wavelengths. (b) Zoomed view of fluorescence decay profiles (λex = 340 nm) of
nanoparticle dispersions at different emission wavelengths. (c) Time-resolved emission
3
Fig. 3 (a) Emission spectra of TPDC-BZ solution in (i) toluene, (ii) THF, (iii) CHCl and (iv)
DCM (inset: photographs of TPDC-BZ in the corresponding solvents upon irradiation
with UV light at 365 nm depicting color tunable emission). (b) FESEM image of
nanoparticles; inset: DLS profile of the aqueous dispersion of nanoparticles. (c) Spectral
characteristics of WLE nanoparticle dispersion: (i) absorption, (ii) emission (λex = 340
nm) spectra; inset: photograph of WLE nanoparticles under irradiation at 365 nm. (d)
The chromaticity diagram (CIE 1931) of WLE nanoparticles (x = 0.29, y = 0.32).
(
TRES) spectra of an aqueous dispersion of nanoparticles with the wavelength range
from 400-650 nm and delay time from 54 ps to 7.8 ns. (d) Photographs of (i)
transparent gel coated on a quartz plate and (ii) free standing thin film in day light. (iii)
Gel coated quartz plate and (iv) thin film exhibiting white light emission under UV light.
It is envisioned that constrained environment of (Fig. S17
nanoparticles may facilitate the excitation energy migration found to decrease in WLE nanoparticles (τavg = 1.7 ns)
between the polymer and encapsulated dyes (Fig. S11). WLE compared to that of pristine aqueous dispersion of OPCP (τavg
†). The decay time of donor monitored at 435 nm was
=
nanoparticles were prepared by reprecipitation method 3.1 ns). The average decay time of TPDC-BZ (3.6 ns at 500 nm)
involving OPCP, TPDC-BZ, and perylene red (PR). The optimized and PR (8.4 ns at 600 nm) was increased in WLE nanoparticles
concentration of OPCP (0.4 mM), PR (0.01 mM) and TPDC-BZ compared to respective aqueous dispersions (Table S3
†
). The
0.5 mg mL ) in THF solution was rapidly injected into decay profiles of nanoparticles monitored at the emission
ultrapure water (Millipore MilliQ, resistivity = 18 M cm). The wavelengths of TPDC-BZ and PR show negative pre-
-1
(
ꢁ
FESEM images of nanoparticles revealed nearly spherical exponentials relating to rise time of 300 and 400 ps,
morphology with average particle size ranging from 80-110 nm respectively (Fig. 4b). The rise time correlates closely with the
(
Fig. 3b). The particle size distribution obtained from dynamic shortest decay component of 400 ps of donor OPCP at 435 nm,
light scattering (DLS) measurements resembles that obtained confirming the ET from excited OPCP to TPDC-BZ and PR.
from the FESEM images (Fig. 3b, inset). Time-resolved emission spectra (TRES) further provide an
2
5
The nanoparticle dispersions show absorption maxima at intimate picture of ET processes. TRES were recorded using
40 nm which corresponds to OPCP (Fig. 3c). Upon exciting at 340 nm diode laser. Emission spectra of WLE nanoparticle
40 nm, the nanoparticle dispersion showed broad emission dispersion collected at different delay time is shown in Fig. 4c.
3
3
covering the entire visible region from 400-700 nm (Fig. 3c and The characteristic emission of OPCP at 435 nm is dominant at
S14a ). The photograph of an aqueous dispersion of initial gated time up to 1.15 ns, which arises because of the
†
nanoparticles under the illumination of UV light of 365 nm direct excitation of OPCP. With the increase of delay time,
reveals bright white emission (Fig. 3c, inset). The CIE color emission at 435 nm decreases due to the depopulation of the
coordinates of nanoparticles were found to be x = 0.29, y = excited state. Further, with longer gated time up to 7.8 ns, the
0
.32 (Fig. 3d) with significantly high CRI of 93 (Fig. S14b
absolute quantum yield of WLE nanoparticles was 35%. The corresponding to TPDC-BZ and PR respectively (Fig. 4c and
quantum yield of WLE nanoparticles is higher compared to S18 ). Such correlated decrease of the intensity in blue region
WLE materials involving insoluble porous polymer like TMBPT- and increase in green and red regions with time corroborate
†). The spectrum is mainly dominated by emission at 500 and 600 nm,
†
2
1
19b
Ir-a (5.2%) and CP-CMPw (8.8%) and comparable to that the results obtained from TCSPC measurements and
5b
using MOFs like Ir-MOF (20.4%) and MOF-253 (33%).
The excitation spectra of WLE nanoparticle dispersion
5
a
unambiguously prove the ET from OPCP to TPDC-BZ and PR.
WLE gel was prepared using agarose gelator. Aliquot of
monitored at different emission wavelengths corresponding to nanoparticle dispersion was taken in agarose gelator and was
emission maximum of OPCP, TPDC-BZ and PR revealed a allowed to cool. WLE gel showed broad emission (ꢀꢁ = 14%) in
common peak at 340 nm relating to the absorption maximum the visible region with the characteristic peaks of OPCP, TPDC-
of OPCP (Fig. 4a). This result indicates the ET from OPCP to BZ, and PR (Fig. 1 and S19a
TPDC-BZ and PR. Further, the processes were investigated by 0.31, y = 0.28 with CRI value of 79 (Fig. S19b and c
time-correlated single photon counting (TCPSC) measurements excitation spectra revealed that the Förster type resonance
†
) having CIE coordinates of x =
†
). The
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energy transfer (FRET) is retained in the gel (Fig. S19d
Journal Name
†
). TRES
6
7
Q. W. Zhang, D. Li, X. Li, P. B. White, J. Mecinović, X. Ma, H.
Ågren, R. J. M. Nolte, H. Tian and H. Tian, J. Am. Chem. Soc.,
measurement was also substantiated the same. The temporal
evolution of peaks at 500 and 600 nm with a concomitant
2
016, 138, 13541.
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,
decrease of emission at 435 nm was observed (Fig. S20†).
4
Solution processable polymers and hybrid materials with
excellent white light emission are important for device
fabrication. Therefore, the thin film was fabricated by coating
the WLE gel on a quartz plate (Fig. 4d). Remarkably, the entire
thin film was highly transparent with a transmittance of 95-
8
9
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97% in 500-800 nm (Fig. S21†) and showed strong white light
emission under the illumination of UV light (Fig. 4d). The
transparent thin film was peeled off from the substrate to
obtain the free-standing WLE thin film (ꢀꢁ = 8%, Fig. 4d). The
CIE coordinates of WLE thin film (0.33, 0.32) is very close to
that of pure white light with CRI value of 82 and CCT 5481 K
1
0 N. B. McKeown and P. M. Budd, Chem. Soc. Rev., 2006, 35
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1,
8
19; (b) C. Yang, B. C. Ma, L. Zhang, S. Lin, S. Ghasimi, K.
(
Fig. S22 and Table S4†).
In summary, TPDC-BZ, a new soluble porous organic
Landfester, K. A. I. Zhang and X. Wang, Angew. Chem. Int.
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2 S. Bandyopadhyay, A. G. Anil, A. James and A. Patra, ACS
Appl. Mater. Interfaces, 2016, 18, 27669.
2
-1
polymer having surface area of 610 m g , high H
3
capacity (143 cm g ) and strong color-tunable emission was
2
uptake
1
-1
fabricated. The highly photoluminescent white light emitting 13 B. C. Ma, S. Ghasimi, K. Landfester, F. Vilela and K. A. I.
Zhang, J. Mater. Chem. A, 2015, 3, 16064.
solution, nanoparticles, gel and transparent thin film were
obtained by encapsulating suitable dyes in the polymer matrix.
The CIE coordinates for the WLE materials were very close to
1
4 (a) L. L. Chen, Y. Honsho, S. Seki and D. Jiang, J. Am. Chem.
Soc., 2010, 132, 6742; (b) K. V. Rao, R. Halder and T. K. Maji
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0074.
(
,
1
nanoparticles was found to be as high as 35%. The underlying
energy transfer phenomenon was elucidated using time-
resolved emission spectra analysis. Compared to existing WLE
systems based on porous solids including MOF and porous
1
6 L. Hao, J. Ning, B. Luo, B. Wang, Y. Zhang, Z. Tang, J. Yang, A.
Thomas and L. Zhi, J. Am. Chem. Soc., 2015, 137, 219
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polymers (Tables S5 and S6†), TPDC-BZ based hybrid materials
turned out to be very promising in the cost-effective
generation of white light. Moving beyond the gas adsorption
properties, the present study paves the way for novel optical
applications of solution processable porous organic polymers
as potentially useful light emitting materials.
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6
,
Financial support from DST (SB/FT/CS-081/2013), New Delhi and infrastructural
support from IISERB are gratefully acknowledged. PP thanks UGC, SB acknowledges
IISERB and JL and AD thank DST-Inspire for fellowship.
4
1
2
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| J. Name., 2012, 00, 1-3
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