Visualization of Stereoselective Supramolecular Polymers by Chirality-Controlled Energy Transfer

Article abstract of DOI:10.1002/anie.201708267

Chirality-driven self-sorting is envisaged to efficiently control functional properties in supramolecular materials. However, the challenge arises because of a lack of analytical methods to directly monitor the enantioselectivity of the resulting supramolecular assemblies. Presented herein are two fluorescent core-substituted naphthalene-diimide-based donor and acceptor molecules with minimal structural mismatch and they comprise strong self-recognizing chiral motifs to determine the self-sorting process. As a consequence, stereoselective supramolecular polymerization with an unprecedented chirality control over energy transfer has been achieved. This chirality-controlled energy transfer has been further exploited as an efficient probe to visualize microscopically the chirality driven self-sorting.

Full text of DOI:10.1002/anie.201708267

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Accepted Article
Title: Visualization of Stereoselective Supramolecular Polymers via
Chirality Controlled Energy Transfer
Authors: Aritra Sarkar, Shikha Dhiman, Aditya Chalishazar, and Subi J.
George
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201708267
Angew. Chem. 10.1002/ange.201708267
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10.1002/anie.201708267
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Visualization of Stereoselective Supramolecular Polymers via
Chirality Controlled Energy Transfer
Aritra Sarkar, Shikha Dhiman, Aditya Chalishazar and Subi J. George*
Abstract: Chirality driven self-sorting is envisaged to efficiently
control functional properties in supramolecular materials. However, it
faces challenge due to lack of analytical methods to directly monitor
the enantioselectivity of resulting supramolecular assemblies. In this
context, we present two fluorescent core-substituted naphthalene
diimide based donor and acceptor molecules with minimal structural
mismatch and comprising of strong self-recognizing chiral motif, for
sorted supramolecular polymers. Although, various molecular
designs have been reported to modulate the energy transfer
process in supramolecular assemblies,[9,10] a chirality based
approach to control energy transfer is seldom reported. [11,4b]
solely chirality to determine the self-sorting process. As
a
consequence, stereoselective supramolecular polymerization with an
unprecedented chirality control over energy transfer has been
achieved. This chirality controlled energy transfer has been further
exploited as an efficient probe to visualize microscopically the chirality
driven self-sorting.
Naturally occurring systems have an extraordinary ability to
competently discriminate between self and non-self from complex
mixtures of similar structural motifs. Moreover, biological systems
such as enzymes and proteins can chirally recognize between the
two enantiomers via supramolecular interactions to facilitate
biological processes.[1] Inspired by this, structural mismatch[2] and
pH variation[3] driven self-sorting process has been investigated
in synthetic supramolecular assemblies. This has been exploited
further to control organization in functional supramolecular
assemblies to modulate their resultant properties.[2] For example,
in chromophoric assemblies, the self-sorting process is utilized to
modulate their opto-electronic properties[2] and its spectroscopic
properties are often used to probe these assemblies.[4] More
recently, high resolution microscopic techniques were used to
even visualize the self-sorted supramolecular polymerization.[5]
However, bio-inspired chirality driven self-sorting systems
have been rarely investigated.[6] In this context, chirality driven
self-sorting of enantiomeric monomers has been exploited to
achieve stereoselective supramolecular polymerization.[7] Our
group has also shown the chirality driven self-sorting of donor (D)
and acceptor (A) supramolecular polymers to control the charge-
transfer properties between the chromophores.[8] However, the
scarceness of chirality based self-sorted supramolecular
assemblies can be attributed to the dynamicity of these
assemblies, which results in low level of chiral differentiation and
lack of analytical methods to characterize them. In this
communication, we present a chirality driven control on the self-
sorting characteristics of supramolecular fibers to modulate their
energy transfer properties and thereby the resulting optical
properties. Furthermore, we have utilized the chirality controlled
energy transfer as an efficient probe to spectroscopically
investigate and to visualize the resulting co-assembled and self-
Figure 1. a) Molecular structures of donor SS-diOEt and acceptors RR/SS-
OEtiPa. b) Schematic representation of chirality controlled co-assembly and
self-sorting and resultant chirality controlled energy transfer process.
Our group has previously reported the stereoselective
supramolecular polymerization of D-A charge-transfer assemblies,
using trans-1,2-bis(amido)cyclohexane (BAC) as strong chiral
self-recognizing motif.[12] In the present study, we have modified
the D and A chromophoric components into a Förster resonance
energy transfer (FRET) pair for a chirality controlled energy
transfer, which we further employ for the visualization of
stereoselective supramolecular polymerization. The two key
requirements for an efficient chiral recognition driven energy
transfer are: i) a minimum structural mismatch between the
chromophores for chirality to control the self-sorting process and,
ii) well-separated optical properties of D and A. To fulfill the
requirements, we chose core-substituted naphthalene diimide
(NDI) derivatives as fluorescent chromophores. For this,
naphthalene diimides were appropriately core substituted, with
both side -OEt (ethoxy) as a green emissive donor chromophore
and with unsymmetrical core-substitution with -OEt and –iPa (N-
isopropyl amine) groups for the red-emissive acceptor
chromophore (Fig. 1a). The donor was tethered in (S,S)-chiral
BAC core (SS-NDI-OEt), whereas the acceptor NDI derivative
was tethered in both (R,R) and (S,S)-chiral cores of BAC (RR/SS-
NDI-OEtiPa) to investigate the chiral self-sorting process (Fig. 1b).
The donor and acceptor NDI derivatives were synthesized and
characterized (Scheme S1 to S4) by NMR and mass spectrometry.
Although, core-substituted naphthalene diimides (cNDIs)
are well studied for their tunable optical and electron transfer
properties,[13] their self-assembly has not been well investigated
A. Sarkar, S. Dhiman, A. Chalishazar and Prof. S. J. George
Supramolecular Chemistry Laboratory, New Chemistry Unit
Jawaharlal Nehru Centre for Advanced Scientific Research
(JNCASR), Jakkur, Bangalore, India-560064
E-mail: george@jncasr.ac.in; Web: www.jncasr.ac.in/george
Supporting information (SI) for this article is given via a link given at the
end of this document.
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Fig. 2. Self-assembly of SS-diOEt (top panel) and SS-OEtiPa (bottom panel): Composition dependent a), e) Normalised absorption spectra and b), f) Normalised
emission spectra (λex = 415 nm for SS-diOEt and 430 nm for SS-OEtiPa), c), g) CD spectra in molecularly dissolved (TCE) and self-assembled states (TCE/MCH).
c) also shows the LD spectrum of SS-diOEt and g) also shows the mirror image CD spectra of both enantiomer SS-OEtiPa and RR-OEtiPa and d), h) TEM images
showing 1-D nanofibers in aggregated 25/75 and 1/99 (v/v) TCE/MCH solutions respectively. Insets of b) and f) show the photographs of the corresponding
molecularly dissolved (left) and self-assembled (right) solutions under UV-light (365 nm irradiation) ([SS-diOEt] = [SS-OEtiPa] = RR-OEtiPa= 2.5x10-5 M).
so far. Thus, we first investigated the self-assembly of the
individual D and A molecules. SS-diOEt and SS-OEtiPa exists in
molecularly dissolved state in polar solvents such as 1,1,2,2-
tetrachloroethane (TCE) which is signified by sharp vibronic
features at 347 nm and 367 nm in the absorption spectrum (Fig.
2a,e, S1, S4). Upon introducing non-polar solvents like
methylcyclohexane (MCH), their self-assembly is induced which
is depicted by the broadening of absorption spectra and reversal
in intensity of vibronic features of the π-π* band at 347 nm and
367 nm (Fig. 2a,e, S1-S6). The assembled state (25/75 (v/v)
TCE/MCH) SS-diOEt emission spectra shows a new red-shifted
emission band at 516 nm in comparison to 502 nm band in
molecularly dissolved state (TCE) (Fig. 2b, S2-S3). A similar red
shift from 591 nm to 641 nm is observed in SS-OEtiPa assembly
(Fig. 2f, S5-S6). Lifetime decay profiles of SS-diOEt assembly
(6.89 ns) shows increased lifetime than that of the corresponding
lifetime of monomer in TCE (1.78 ns) (Fig. S7a, Table S1), which
along with the excitation spectra (Fig. S2) suggests the formation
of fluorescent J-aggregates. However, lifetime decay profile of the
SS-OEtiPa assembly showed a sharp decay component (1.89 ns)
in comparison to monomeric state (10.96 ns) suggesting
formation of J-aggregates with an efficient excitonic migration in
the stacks (Fig. S7b, Table S2).[14,9a]
FE-SEM (Fig. 2d,h, S8, S9). The fluorescent nature of these
assemblies were further confirmed by confocal microscopy that
shows green and red fluorescent 1-D nanofibers of SS-diOEt and
SS-OEtiPa, respectively (Fig. S8, S9).
Spectoscopic investigations revealed sufficient spectral
overlap of self-assembled SS-diOEt emission and RR/SS-
OEtiPa absorption spectra which is necessary to obtain an
efficient energy transfer (Fig. S10a). Moreover, our previous study
on BAC based D-A system suggest that due to strong hydrogen
bonding between the chiral BAC motif, there is significant energy
difference between homochiral and heterochiral stacks. Hence,
we envisage to study the effect of chirality to determine the self-
sorting behavior of present D and A system and to use FRET as
a probe to spectroscopically and microscopically discriminate
between chirality driven self-sorted and co-assembled D and A
assemblies.
First we investigated the spectroscopic properties of the
homochiral mixture of D and A molecules. To avoid any kinetic
traps, all the samples were annealed by heating and cooling prior
to measurements. Upon excitation of donor at 415 nm in a
solution of SS-diOEt (c = 2.5x10-5 M, 25/75 (v/v) TCE/MCH) and
0.2 % SS-OEtiPa shows a significant quenching of donor
fluorescence at 516 nm and buildup of acceptor emission at 591
nm (Fig. 3a). Increase in acceptor percentage beyond 0.2% does
not result in further quenching of donor emission, suggesting
saturation of energy transfer process with mere 0.2 % of acceptor.
This indicates an efficient co-assembly of D and A molecules and
a very efficient energy transfer in these homochiral stacks, which
is also confirmed by the excitation spectra (Fig. S10e). The
indirect excitation of the acceptor at 415 nm in the homochiral
mixture showed emission at 591 nm corresponding to its
monomeric emission, suggesting that the acceptors is distributed
in the stack as isolated molecules. Moreover, the direct excitation
of the A at 550 nm shows a much lesser intensity than that by
indirect excitation at 415 nm indicating an amplified emission via
Although, SS-diOEt exhibited a positive bisignated CD
signal in the monomeric state (in TCE), characteristic of
intramolecular excitonic coupling in bischromophoric assemblies,
the CD signal of the corresponding self-assembly is highly
contaminated with the contribution of linear dichroism (LD)
suggesting the presence of long aligned supramolecular fibers
(Fig. 2c). However, CD spectra of RR- and SS-OEtiPa show
mirror image bisignated CD signal in both molecularly dissolved
and self-assembled state (Fig. 2g), suggesting the presence of
both intramolecular and intermolecular excitonic coupling.
The morphological investigations into D and A assemblies
show that both of them form 1-D fibers as visualized by TEM and
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Figure 3. Energy-transfer probing of chiral self-sorting: Top panel corresponds to solution of SS-diOEt and SS-OEtiPa whereas bottom panel corresponds to
the solution of SS-diOEt and RR-OEtiPa a), e) Emission spectra and corresponding confocal microscopy images collected by b), f) Channel I (480-560 nm), c), g)
Channel II (570-620 nm) and d), h) Merged Channel I and II. a) Co-assembly of SS-diOEt and SS-OEtiPa depicted by quenching in donor and amplified acceptor
emission that show FRET. b-d) Confocal microscopy images with 0.2 % SS-OEtiPa. b) Shows SS-diOEt green fluorescent fibers, c) shows energy transfer to
incorporated SS-OEtiPa acceptor in donor stacks and d) merged image depicting spatial overlap of fibers emitting green and red emission confirming co-assembly
and energy transfer. e) Self-sorted assemblies of SS-diOEt and RR-OEtiPa depicted by negligible changes in donor and acceptor emission. f-h) Confocal
microscopy images with 1 % RR-OEtiPa. f) Shows SS-diOEt green fluorescent fibers, g) shows absence of red emitting species and absence of energy transfer
and h) merged image depicting presence of solely SS-diOEt green emitting fibers. Note: Insets of a) & e) shows the corresponding photographs of the donor and
acceptor mixture under UV-light (365 nm irradiation), ([SS-diOEt] = 2.5x10-5 M, 25/75 (v/v) TCE/MCH))
energy transfer (Fig. 3a).
orange emission, when viewed though channels I and II (Fig. 3b,c,
S12). On merging them, we observe a perfect overlay of the two
colours which confirms that the emission originates from the same
fibers confirming co-assembled fibers of D and A molecules, via
stereoselective supramolecular polymerization (Fig. 3b-d, S12). A
similar observation was concluded in fluorescence microscopic
images (Fig. S13).
We next investigated the D and A mixture of opposing
chirality, SS-diOEt and RR-OEtiPa, to see the effect of chirality
on assembly characteristics. A solution of SS-diOEt (c = 2.5x10-5
M, 25/75 (v/v) TCE/MCH) with upto 30 % RR-OEtiPa, on
excitation at 415 nm, did not result in any significant quenching of
donor emission suggesting the absence of energy transfer
process, which also suggests a chirality driven self-sorting of D
and A assemblies (Fig. 3e). The energy transfer process was
further validated by time-resolved fluorescence measurements.
Homochiral, co-assembled solutions of SS-diOEt and SS-OEtiPa
show decrement in lifetime of donor and enhancement in lifetime
of acceptor (Fig. S10b,c, Table S3-S4) whereas chiral self-sorted
assemblies of SS-diOEt and RR-OEtiPa do not show any change
in donor and acceptor lifetime, compared to the individual
homochiral stacks of D and A molecules (Fig. S10d, Table S5-S6).
The enatioselectivity of SS-diOEt towards SS-OEtiPa over RR-
OEtiPa was calculated to be 98.6% (Fig. S11).
Figure 4. Visualization of self-sorted fibers of 1:1 mixture of SS-diOEt and
RR-OEtiPa. Fluorescence microscopy images obtained by a) Excitation at the
donor absorption using GFP (BP 470/40) filter and collection at donor emission
showing green fluorescent domains, b) excitation at acceptor absorption using
TX2 (BP 560/40) filter and collection at acceptor emission showing red
fluorescent domains and c) merged image showing separate domains with no
overlap of green and red domains. ([SS-diOEt] = 2.5x10-5 M, [RR-OEtiPa] =
2.5x10-5 M, 1/99 (v/v) TCE/MCH.)
Next we visualized this chirality driven co-assembled and
self-sorted supramolecular polymers microscopically using
energy transfer as a probe. The confocal images of various
solutions dropcasted on glass slide were imaged. The donor was
excited at 458 nm and the emission was collected in two channels,
channel I for 480 to 560 nm and channel II for 570 to 610 nm
emissions, corresponding to green and orange/red emission
respectively. The solution of SS-diOEt (c = 2.5x10-5 M, 25/75 (v/v)
TCE/MCH) and 0.2 mol% SS-OEtiPa showed fibers of green and
In contrast, the solution of SS-diOEt (c = 2.5x10-5 M, 25/75
(v/v) TCE/MCH) and 1 mol% RR-OEtiPa showed only presence
of green fibers on excitation of donor band at 458 nm (Fig. 3f-h,
S12). No orange/red emissive species were obtained due to
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Acknowledgements
We thank Prof. C. N. R. Rao, FRS for his support and guidance,
JNCASR, Department of Science and Technology, Government
of India and Shekh Saqr Laboratory (SSL) for financial support
and Prof. J. Haldar and Dr. S. Samaddar, JNCASR for
fluorescence microscopy measurements.
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Keywords: Chirality • Self-sorting • Stereoselective
supramolecular polymerization • Energy transfer • Self-assembly
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Entry for the Table of Contents
COMMUNICATION
Visual discrimination of self-sorted
and co-assembled stereoselective
supramolecular polymers is presented
using chirality-controlled energy
transfer.
Aritra Sarkar, Shikha Dhiman, Aditya
Chalishazar and Subi J. George*
Page No. – Page No.
Visualization
of
Stereoselective
Polymers via
Supramolecular
Chirality Controlled Energy Transfer
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