Cascade energy transfer and tunable emission from nanosheet hybrids: Locating acceptor molecules through chiral doping

Article abstract of DOI:10.1039/c7cc02994b

Light harvesting donor-acceptor assemblies are indispensable to efficiently tap photons. In an attempt to improve the light harvesting efficiency of an acceptor doped assembly, we design and synthesize a donor-acceptor-donor triad which exhibits an except

Full text of DOI:10.1039/c7cc02994b

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Cascade Energy Transfer and Tunable Emission from Nanosheet
Hybrids: Locating Acceptor Molecules Through Chiral Doping
Goudappagouda, a,b Vivek Chandrakant Wakchaure,a,b Kayaramkodath Chandran Ranjeesh,a,b
Chalona Antony Ralph Abhai,c Sukumaran Santhosh Babua,b*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Light harvesting donor-acceptor assemblies are indispensable to subsequently became the active components in electronic
efficiently tap photons. In an attempt to improve the light devices and other related applications.6
harvesting efficiency of an acceptor doped assembly, we design
Cascade energy transfer (CET) is highlighted as a unique
and synthesize a donor-acceptor-donor triad which exhibit an phenomena involving active participation of individual
exceptional intramolecular energy transfer with excellent components to direct energy towards the most suitable
efficiency. Moreover, a facile cascade energy transfer (energy acceptor moiety and hence to tune the emission color from
funnelling) is observed in the presence of a series of second blue to red or even white.7-9 However, most of the reported
acceptors (63-91% efficiency) with tunable emission colours. Self- CET systems are complex and exhibit best performance in
assembled nanosheets formed by the triad in the presence of solution or gel state which limits further demonstration of
acceptors, exhibit cascade energy transfer assisted tunable these materials.8,10 In the recent past, many research groups
emission. In addition, use of chiral acceptors induce chirality to have focused on CET in multichromophoric assemblies
the triad and results in the formation of chiral nanosheets along equipped with energetically favourable and suitably placed D-
with cascade energy transfer. Here chiral induction, nanosheet
A
units.7,8 Research groups of Fréchet and Müllen
formation and cascade energy transfer in the presence of chiral independently demonstrated sequential ET in dendritic
acceptor is used as a tool to probe the intercalation of acceptor multichromophoric systems.8 In another strategy, the donor
molecules in the donor scaffold.
scaffolds are doped with acceptors to facilitate energy
transfer.5d However, a clear evidence for the location of
acceptor molecules in the doped energy transfer systems is
nearly impossible. In the context of favourable donor-acceptor
distance for efficient energy transfer, probing the acceptor
location in donor matrix is always desirable to improve design
strategies. Here we report efficient intramolecular ET in a
donor-acceptor-donor (D-A-D) triad DADT, which exhibit CET
assisted tunable emission with various second acceptors.
Chiral acceptors enabled to locate the acceptors in the hybrid
assembly and thereby to reveal the reason for efficient
cascade energy transfer.
The focus on alternate energy sources has aroused interest
in the development of new organic functional assemblies for
solar light harvesting and conversion.1 Natural as well as
artificial light-harvesting systems utilize ordered chromophore
arrays to efficiently and unidirectionally transfer absorbed
radiation.2 In these assemblies, chromophores are placed at
optimum distances with appropriate orientations in space
using specific noncovalent interactions.3 By mimicking natural
photosynthetic system, numerous studies using artificial
analogues focusing on self-assembled multichromophoric
arrays are reported.2c,d,4a In this direction, dendrimers, gels,
polymers, organic-inorganic hybrids etc. have been widely
investigated for energy transfer (ET) studies.4 Intriguingly,
tailor-made organic donor-acceptor (D-A) assemblies have
attracted wide attention due to favourable ET features5 and
Absorption spectrum of DADT (Figure 1a, Scheme S1, S2) in
dichloromethane (DCM) solution, shows peaks corresponding
to the donor (TPE) and acceptor (BPA) moieties having maxima
at 320, 450 and 472 nm (Figure 1b). Emission spectrum
consists of major contribution from BPA with a maximum
located at 492 nm (Figure 1c, S1) and a minor TPE emission
(Figure S2; inset). A thin film of DADT has shown a broad, red
shifted absorption and emission spectra, indicating aggregate
formation on surface (Figure 1b, 1c). The disappearance of TPE
emission in DADT thin film points to possible ET between TPE
and BPA in the triad and hence justifies the molecular design
a.Organic Chemistry Division, National Chemical Laboratory (CSIR-NCL), Pune-
411008, India.
b.Academy of Scientific and Innovative Research (AcSIR), New Delhi-110020, India.
c. School of Chemical Sciences, Mahatma Gandhi University, Kottayam-686560,
India.
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any
supplementary information available should be included here]. See
DOI: 10.1039/x0xx00000x
(Figure 1c). A good spectral overlap integral (J(λ
) = 2.67 x 1013
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(solution) and 3.22 x 1013 (thin film) M-1cm-1nm4) exists nm due to contributions from three different chromophore
between TPE emission and BPA absorption, which allows the units (Figure S7), emission spectrum shows complete
triad to efficiently transfer energy from TPE to BPA (Figure 1d, quenching of TPE and moderate quenching of BPA emissions
S2).11 Wavelength dependent emission lifetime decay profile when DADT is excited at 340 nm (λmax of TPE absorption) in
of BPA in DADT thin film shows a faster decay at the lower the presence of the acceptors (Figure 2a, 2b, S8). ET in DADT
wavelengths than the longer wavelength emission of BPA, thin films with second acceptors was found to be extremely
indicating the presence of strong energy migration among efficient and an optimum ET performance was observed at 10
(BPA of DADT) aggregates after energy transfer (Figure 1e). An mol% of the acceptors. Interestingly, a CET with strong second
efficient ET with almost complete disappearance of the donor acceptor emission from 550 to 700 nm was observed upon
emission in DADT could be ascribed to, i) optimum Förster exciting the TPE unit of DADT. This could be attributed to the
distance in the covalently linked D-A units (centre to centre sequential ET from TPE to BPA and then to the second
distance of ~2 nm) and ii) high spectral overlap integral acceptor molecules. The energy gradient present in three
between TPE emission and BPA absorption. Since the donor chromophores enabled a stepwise ET from the high to the low
emission is absent both in solution and thin films, ET energy absorbing molecules.
experiments were cross checked with that of
and their physical mixture (2:1) (Figure S3, Table S1).
Compared to and , solution and thin film of the physical
mixture showed a weak energy transfer, keeping the donor
emission still active. In contrast to , a complete donor
1, 2 (Scheme S3)
1+2
1
2
1+2
fluorescence quenching in DADT ascertains the significance of
optimum D-A distance favouring ET. Time-resolved
experiments of DADT thin films on nanosecond timescale
indicated a faster triexponential decay with a lifetime of 0.43
ns (18.70%), 1.8 ns (51.79%) and 8.6 ns (29.51%) (Figure S4,
Table S1). An increase in the lifetime of BPA moiety in DADT
thin film compared to that of 2 supports ET in DADT (Table S1).
Fig. 2. Emission spectrum of DADT thin films with varying amounts of (a) DPP and (b)
RB (λex = 340 nm). (c) Photograph of DADT-RB thin films with varying amounts of RB
under UV light (365 nm). Fluorescence lifetime decay profile of DADT thin film with
increasing amounts of (d) DPP and (e) RB (λex = 374 nm, λmon = 526 nm). Insets show
the fluorescence lifetime decay profile of the acceptors in the absence (O) and
presence (Δ) of DADT, monitored at 580 nm for DPP and 600 nm for RB.
The efficient ET in thin films could be due to favourable
aggregate formation assisted energy migration in thin films as
well as the conformational flexibility provided by the alkyl
linker between BPA and TPE, which brings the ET partners in
close proximity.12 ET efficiency among the second acceptors is
varied as 91%, 63%, 78%, 77% and 70% for DPP, RB, PBI-1, NR
and RBn, respectively (Figure 2a, 2b, S8). The relatively
quenched emission of the acceptors exhibited enhanced
emission due to sensitization via energy transfer (for instance,
NR). By taking DPP into consideration as the best acceptor
candidate, excitation of TPE at 340 nm results in
intramolecular ET efficiency of ~99%7b and out of that, 91% of
energy is intermolecularly transferred to DPP. Upon increasing
the amount of acceptors, a reasonably efficient CET resulted in
tunable emission color from green (0 mol%) to yellow (3
mol%), brown (7 mol%) and red (10 mol%) (Figure 2c). Even
though, there have been various methods to obtain tunable
emission,13 one such study using an ET efficient triad and
varieties of other acceptors has rarely been attempted.
Fig. 1. (a) Chemical structure of DADT. Normalized (b) absorption and (c) emission
spectra of DADT in DCM solution and thin film ( ex = 320 nm for solution and 340 nm
λ
for thin film). (d) Spectral overlap integral between emission of 1 and absorption of BPA
of DADT in thin film. (e) Wavelength dependent fluorescence lifetime decay profile of
DADT thin film (λex = 374 nm, IRF = instrument response function). Inset shows the
fluorescence lifetime decay profiles of DADT thin film monitored at 490 nm (O) and at
600 nm (Δ), showing growth at the initial time scale.
Second acceptor molecules such as diketopyrrolepyrrole
(DPP), Rhodamine B (RB), perylenebisimide (PBI-1), Nile red
(NR) and Rubrene (RBn) derivatives (Scheme S4) having good
spectral overlap integrals of their absorption peaks with DADT
emission are chosen for energy tapping (Figure S5, S6). Even
though the thin film absorption spectrum covers 300 to 650
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Fluorescence lifetime decay of the BPA emission was structures were formed by DADT-DPP coassembly also (Figure
considerably decreased with increasing amounts of the second S23).
acceptors and thus ruled out the trivial ET mechanisms (Figure
2d, 2e, S9, Table S3). In addition, a temporal growth observed
for fluorescence lifetime decay of second acceptors (for
instance, insets of Figure 2d, 2e for DPP and RB, respectively),
in the presence of DADT at an early time scale also points to
the initial singlet excited state population build-up before
radiative decay associated with Förster ET. In the case of
second acceptors, wavelength of excitation with minimum
absorption was chosen to minimize the contribution of direct
excitation towards ET assisted emission (Figure S10). As
anticipated, the ET efficiency in solution was very low
compared to that of thin films (Figure S11, S12). ET studies
were conducted in different concentrations of DADT in DCM
(eg. 1x10-5 and 5x10-5 M) and exhibited consistent results.
Since our main focus is thin films of DADT prepared from 1
mM DCM solution, all energy transfer studies in solution were
Fig. 3 (a) OM and (b) TEM images of DADT-PBI-1 hybrid nanosheets. Elemental
conducted at the same concentration.
mapping of the hybrid sheets for (c) carbon, (d) nitrogen and (e) oxygen. (f) AFM image
The excellent ET in thin films inspired us to know about the
D-A interactions, however, it is extremely challenging to detect
that in thin films. Hence self-assembly of DADT was monitored
of the DADT-PBI-1 hybrid sheet with (g) height profile for the marked line in the AFM
image.
by adding DCM solution to excess methanol, typically, 10 ꢀL
In order to locate the acceptor intercalation in hybrid
nanosheets, CET has been attempted in a D-A assembly of
DADT and chiral acceptors. Similar to PBI-1, CET was observed
in DADT-PBI-2R/S (Scheme S5) in solution (Figure S24-S27) as
well as in thin films (Figure S28, S29, Table S4). In addition,
DADT formed chiral nanosheet assembly in the presence of
PBI-2R and PBI-2S (Figure S30, S31). Surprisingly, circular
dichroism (CD) spectra of DADT-chiral PBI assembly showed
exciton coupled mirror image CD spectra with an enhanced CD
DCM solution (1 mM) of DADT was added to 3 mL of MeOH
and the resulting aggregate solution was drop casted on Silicon
substrate for analysis. In the presence of second acceptors
such as PBI-1 and DPP (up to 10 mol%), DADT exclusively
formed nanosheet structures in large numbers (Figure 3).
However, DADT, PBI-1 and DPP alone form ill-defined random
structures under similar experimental conditions (Figure S13,
S14). DADT assembly formation is efficient up to 10 mol% of
PBI-1 loading and further addition resulted in phase
separation. The presence of PBI-1 in the nanosheets is
confirmed by the characteristic red emission of PBI-1, when
the nanosheets are excited at 352 nm and monitored in the
red window, 573 nm in fluorescence imaging (Figure S15). The
optical microscopy (OM) (Figure 3a), transmission electron
microscopy (TEM) (Figure 3b, S16) and scanning electron
microscopy (SEM) (Figure S17) images showed the presence of
layered nanosheets. Elemental mapping for carbon, nitrogen
and oxygen confirmed the uniform distribution of PBI-1
throughout the nanosheets (Figure 3c-e). Detailed AFM
imaging showed the presence of nanosheets with varying
heights in multiple of 5 nm (Figure 3f, 3g, S18, S19) and this
might be due to the extended aggregation of initially formed
monolayer assembly (~5 nm height) (Figure S20). The
formation of nanosheets was monitored with time and
immediate drop casting of the solution showed that nanosheet
formation is spontaneous (Figure S21). Thus formed
nanosheets grow in size and height with time and optical
microscope images confirmed the formation of larger
nanosheets upon ageing (Figure S21). XRD profile of the sheets
showed two peaks with d-spacing of 3.39 and 4.06 Å, might be
intensity for π-π* transition of TPE (λmax = 315 nm) in DADT
(Figure 4a), indicating the preferable intercalation of chiral
PBIs in the TPE region of DADT layered sheet assembly (Figure
S32) and leading to chiral induction at that particular
absorption part (Figure 4a, 4b).14 Both reduced energy transfer
efficiency (Figure S33), layered hybrid sheet formation and CD
signal at the TPE absorption region points to possible selective
interaction of chiral PBIs within TPE units and placing it in a
geometrically unfavourable position for energy transfer to
BPA. In short, energy transfer and self-assembly studies of
DADT with chiral PBIs strongly support the possibility of
intercalation of the second acceptor molecules in the
interlayer region of nanosheet hybrids (Figure S32). The
specific intercalation of PBIs in the locking cites of TPE is
supported by the AFM images with varying heights. The
initially formed single layer assemblies are joined together by
the intercalated PBIs. Even though the CD signal enhancement
is not remarkable, it enables to point out the possible
intercalation mode of acceptor molecules. Hence chiral PBIs
act as a probe to monitor the location of acceptor molecules in
the donor scaffold. The overall processes involving CET
assisted tunable emission and chiral induction of DADT and
second acceptor assemblies is schematically demonstrated in
Figure 4c. We strongly believe that CET and chiral induction in
a multi-fluorophoric assembly is a rare observation and this
due to the intermolecular π-stacking distance between central
BPA moieties in the same layer and interdigitating TPE
moieties of adjacent layers (Figure S22). Similar nanosheet
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a series of second acceptors with good spectral overlap
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Acknowledgements
Goudappagouda, VCW and KCR acknowledge UGC, India for
fellowship. We thank Prof. H. N. Gopi, IISER Pune for CD
spectral measurements. This work is supported by SERB Govt.
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