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Journal of Luminescence 210 (2019) 371–375

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Journal of Luminescence
journal homepage: www.elsevier.com/locate/jlumin

Tuning the fluorescence behavior of liquid crystal molecules containing T


Schiff-base: Effect of solvent polarity
Ashok K. Satapathya,b, Santosh K. Beherac, Ankit Yadavd, Laxmi Narayan Mahourd,
C.V. Yelamaggade, K.L. Sandhyab,∗∗, Balaram Sahood,∗
a
Department of Physics, Acharya Institute of Technology, Bangalore, 560107, India
b
Department of Physics, Ramaiah Institute of Technology, Bangalore, 560054, India
c
Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore, 560012, India
d
Materials Research Centre, Indian Institute of Science, Bangalore, 560012, India
e
Centre for Nano and Soft Matter Sciences, Jalahalli, Bangalore, 560013, India

A R T I C LE I N FO A B S T R A C T

Keywords: We report the influence of intermolecular and intramolecular hydrogen bonding on the excited state proton
Bent-core liquid crystals transfer (ESPT) emission behavior of two bent core liquid crystal (BLC) molecules, C54H63NO9 (BLC3) and
Intramolecular hydrogen bond C60H75NO9 (BLC4), having a Schiff-base and two long alkyl chains at its two ends. Fluorescence spectra of these
Intermolecular hydrogen bond BLC molecules dispersed in different solvents show dual emission (at ∼ 365 nm and ∼425 nm) from the keto and
ESPT
enol tautomers. We observed that the population of these keto and enol tautomers and the corresponding in-
Effect of solvents
Photoluminescence
tensities of fluorescence emission are strongly influenced by the solvent polarity. In protic solvents, formation of
intermolecular hydrogen bond with the Schiff-base of the BLC molecules is highly favoured than the in-
tramolecular hydrogen bonding. This intermolecular hydrogen bonding drastically reduces the population of the
keto tautomers in the excited state, resulting in enhanced enol fluoroscence band along with a weak keto emission
band. The observed intensity of the enol fluorescence band is the highest for the most studied polar solvent
(methanol). On the other hand, in aprotic solvents, the intramolecular hydrogen bonding is highly favoured,
which leads to the formation of keto tautomers in the excited state. Hence, an intense keto emission band is
observed for the aprotic solvents along with a weak enol emission band. From the time resolved fluorescence
studies we observed a longer life time for the keto band than that for the enol band. This is also related to the
delayed emission associated with the vibrational bands resulting from the bulky alkyl chains attached to the ends
of the BLC molecules.

1. Introduction enol and excited keto tautomer. The notable properties of the ESIPT dyes
are dual emission, large Stokes shift and ultrafast processes. ESIPT dyes
In recent time photophysical studies of dual emitters remain a very have found applications in many fields such as in chemosensors, elec-
active field of research. These dyes found emerging applications in troluminescent materials, laser dyes, and UV-photostabilisers, white
biological and chemical systems due to red shifted emission which is organic light-emitting diodes (OLED) [17–22]. The spectral properties
highly Stokes shifted [1–12]. In this category, dyes undergoing an ex- of the ESIPT dyes depend mainly on hydrogen bonding, rotamerisation
cited-state intramolecular proton transfer (ESIPT) are chiefly attractive. process and pH of the surrounding medium and the substituents present
ESIPT is a very fast phototautomerisation process taking place along an on donor and acceptor units [23–27]. The fluorescence properties of the
intramolecular hydrogen bond between proton donor and proton ac- ESIPT fluorophores are tunable by changing these parameters. Several
ceptor and that are significantly tuned upon electronic excitation series of compounds undergo ESIPT and they have been investigated
[7,13–17]. The pre–requisite for ESIPT is the presence of intramolecular with both experimental and theoretical approaches [14,28–32]. How-
hydrogen bond between proton donor (–OH and –NH2) and proton ever, the effect of hydrogen bonding on proton transfer process can be
acceptor (=N– and –C]O) groups near each other in a molecule. ESIPT used to tune the excited state emission properties of various dyes, which
usually results in dual fluorescence with emission from both excited attracts a lot of attention [15]. Zhou et al. reported the effects of


Corresponding author.
∗∗
Corresponding author.
E-mail addresses: klsandhya@msrit.edu (K.L. Sandhya), bsahoo@iisc.ac.in (B. Sahoo).

https://doi.org/10.1016/j.jlumin.2019.02.056
Received 22 December 2018; Received in revised form 17 February 2019; Accepted 26 February 2019
Available online 01 March 2019
0022-2313/ © 2019 Elsevier B.V. All rights reserved.
A.K. Satapathy, et al. Journal of Luminescence 210 (2019) 371–375

Fig. 1. Chemical structures of (a) BLC3 and (b) BLC4.

intermolecular hydrogen bonding on the dual fluorescence of methyl


salicylate [33]. They investigated that the intermolecular hydrogen Fig. 2. The structure of the emitting species enol and keto in the excited state.
bond plays an important role for the dual fluorescence of methyl sali-
cylate in alcoholic solvents. Subsequently, the effect of solvent polarity respectively.
on different class of ESIPT dyes including salicylideneaniline, hydroxy-
acetophenones, hydroxyflavones, hydroxyphenyl-oxazole(HPO), hy-
droxyphenyl-benzoxazoles (HPBO), hydroxyphenyl-benzothiazole 3. Results and discussion
(HPBT) and hydroxyphenyl-benzimidazoles (HPBI) were extensively
investigated [14]. Park et al. reported a novel class of ESIPT-active The absorption spectra of BLC3 and BLC4 exhibit multi absorption
molecule forming columnar liquid crystals with enhanced fluorescence bands in n-hexane, i.e., absorption at ∼225 nm, ∼265 nm and
[34]. In this work, we studied the effect of solvent polarity on the fa- ∼315 nm. These band positions remain unaffected with solvent po-
vorability of hydrogen bond formation and the subsequent effect on larity (Fig. S1). The origin of the bands is π-π∗ and/or n-π∗ transitions.
ESIPT behavior of two bent core liquid crystal (BLC) molecules con- The presence of the Schiff-base (C]N) in the BLC molecules allows
taining salicylideneaniline core (Schiff-base) attached with two alkyl the existence of two tautomeric forms in the excited state of the com-
chains at their ends, as shown in Fig. 1. pounds, enol and keto, as shown in Fig. 2. In general, molecules con-
taining proton donor and proton acceptor nearly upon photoexcitation
2. Materials and methods under goes a cyclic process. These two forms can be foreseen to cause
the dual emissive behavior of the compounds as schematically shown in
The chemical structures of the two bent core liquid crystals (BLCs) Fig. 3. The measured fluorescence spectra of both the BLCs are shown in
used for this study, C54H63NO9 (BLC3) and C60H75NO9 (BLC4), are Fig. 4. Clearly, upon photoexcitation at 310 nm, BLC3 and BLC4 emit
provided in Fig. 1. The details of synthetic procedure and the liquid dual emission fluorescence at ∼365 nm and ∼425 nm. We observed a
crystal behavior of these BLCs are reported elsewhere [35]. Both liquid weak-intensity shorter wavelength band (at ∼ 365 nm) and a strong-
crystals are similar in structure except the alkyl groups attached at their intensity longer wavelength band (at ∼ 425 nm) for aprotic solvents (n-
ends. BLC3 constitutes of alkyl groups –C10H21 and –C10H21, whereas hexane and cyclohexane). Note that, n-hexane and cyclohexane have a
BLC4 contains –C10H21 and –C16H33 at their two ends. The UV–Vis very small difference in their polarity (n-hexane: 0.009, cyclohexane:
absorption spectra (Figs. S1 and S2, electronic supplementary in- 0.006, with respect to the reference polarity of water:1.000). However,
formation (ESI) file) of the BLCs were recorded using “Perkin Elmer for less polar cyclohexane we observed an intense longer wavelength
Lambda 750 UV–Visible” spectrophotometer. All the measurements emission band, in comparison to that for n-hexane. On the other hand,
were performed with 1.5 μM concentration of the solute in different in protic solvents (such as methanol, ethanol and 2-propanol) the in-
solvents to avoid aggregation and self-quenching. The HPLC grade cy- tensities of these bands are reversed. As the polarity of the protic sol-
clohexane, n-hexane, 2-propanol, ethanol, methanol are used as sol- vents increase, the intensity of the shorter wavelength emission band
vents for this study, where the polarity of the solvents are 0.006, 0.009, increases. In addition, a marginal blue shift is observed for longer wa-
0.546, 0.654 and 0.762 (with respect to the unity (1.0) polarity of velength band for the protic solvents. This suggests that the longer
water). Fluorescence spectra were recorded using HORIBA Jobin Yvon wavelength emission was due to ESIPT form keto tautomer and shorter
Fluoromax-4 spectrofluorimeter. The concentration of the solute and wavelength band is due to normal emission of excited enol [26].
the solvents used for fluorescence study were same as that of absorption In excited state proton transfer the excited state keto is less polar
study. The fluorescence lifetimes were measured from time-resolved than ground state enol tautomer, as a result, with an increase in polarity
intensity decay by time correlated single-photon counting (TCSPC) of the solvents the energy gap between these states increases leading to
method on an Edinburgh instrument (Life-Spec II) using 303 nm LED. a blue shift. Similar blue shift is also observed for other reported ESIPT
The fluorescence decay was analyzed by deconvolution method using exhibiting molecules. The shorter wavelength band is due to emission
the DAS6 software. The obtained values of χ2 for all the fittings were from excited enol tautomer and the longer wavelength is due to keto
close to 1 and weighted residual values were between +4 and - 4. tautomer formed from excited enol in excited state. The solvent polarity
The fluorescence quantum yields of BLC3 and BLC4 samples were greatly influences the easy formation of keto in excited state.
determined relative to that of quinine sulphate (Φr = 0.546) and cal- The solvent polarity modulation of fluorescence is quite interesting.
culated on the basis of the following equation [36]. It is well studied that keto tautomer are efficiently produced in hydro-
Is Ar ns2 carbon solvents [25–30,37]. In alcoholic (protic) solvent, there exists
Φs
= competition between intramolecular bonding of the nearest hydrogen with
Φr Ir As nr2
the Schiff-base and intermolecular bonding of hydrogen of the solvents with
where Φs is the fluorescence quantum yield of the samples, Is and Ir are the Schiff-base.
the integrated fluorescence area, and As and Ar are the absorbance Therefore, these compounds show different photophysical behavior
values for the sample and reference solutions, respectively. ns and nr are in solutions of different polarities. In aprotic n-hexane, the proton
the refractive indices for the sample and reference solutions, donor -OH group and proton acceptor = N site (Fig. 5 (a)) forms strong

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A.K. Satapathy, et al. Journal of Luminescence 210 (2019) 371–375

Fig. 3. Mechanistic pathways for the fluorescence emission for the keto (produced from cis-enol) and enol (produced from trans-enol) tautomers.

Fig. 5. The scheme of formation of intramolecular and intermolecular hy-


drogen bonding in aprotic and protic solvents, respectively.

be observed (see ESI, Fig. S3 and S4).


The time resolved fluorescence spectra of our BLC3 and BLC4
samples are given in Fig. 6. For understanding the behavior of the BLCs
in protic and aprotic solvents, we have chosen methanol as protic and n-
hexane as aprotic solvent. The decay intensities I(t), shown in (Fig. 6)
clearly shows two decay modes associated with two life times, τ1 and
τ2. Here, the mean life (τ) is the time required for the intensity of
fluorescence to reach a value of ( 1 )th of the initial intensity. The decay
e
curves (Fig. 6) are fit with two separate profiles, as given by the fol-
lowing equation.
−t −t
I (t ) = A + B1 e τ1 + B2 e τ2

The fraction of intensities (in percentage) contributed by the two


Fig. 4. Fluorescence spectra of (a) BLC3 and (b) BLC4 in different aprotic and modes are calculated by:
protic solvents, λexc = 310 nm.
Bi τi
Fi (%) = 2
× 100
∑ j = 1 Bj τj
intramolecular hydrogen bonding, which facilitates the proton transfer
and upon photo excitation it emits strong keto emission. However, in The lifetimes obtained from fitting of the decay curves are given in
protic solvents, the -OH group of the solvents form intermolecular hy- Table 1. It is clear from the table that the lifetime τ1 is always lower
drogen bond with = N site. Hence, in protic solvents, there is favorable than that of τ2, for a particular solvent at a particular emission wave-
formation of intermolecular hydrogen bonding in these BLCs (Fig. 5 length. For both the decay modes (τ1 and τ2) in BLC3 and BLC4, the
(b)). This prevents the ease of (intramolecular) proton transfer and longer wavelength emission band λem = 450 nm has longer lifetime
reduces the keto emission in photo excitation [25]. Their results sum- and the shorter wavelength emission band λem = 365 nm has shorter
marize the weak normal emission (at ∼365 nm) and strong tautomer lifetime. We compare the decay behavior of both the BLCs in protic
emission (at ∼425 nm) in n-hexane and cyclohexane. Likewise, a (methanol) and aprotic (n-hexane) solvents. For both BLCs at
strong normal emission (at ∼365 nm) and weak tautomer emission (at λem = 450 nm, τ2 is lower for protic solvent than aprotic solvent, but at
∼425 nm) in n-hexane and cyclohexane, were observed. Note that due λem = 365 nm, τ2 is longer for protic solvents than aprotic solvents.
to overlapping of the FTIR line positions (at about 3330 cm−1) of NeH Again for both the BLCs, at λem = 365 nm, the value for τ1 for protic
and OeH stretching vibrations, the effect of intramolecular or inter- and aprotic solvents are not very different, but at λem = 450 nm, the
molecular hydrogen bonding in the FTIR absorption spectra could not protic solvents have lower τ1 in comparison to aprotic solvents.

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A.K. Satapathy, et al. Journal of Luminescence 210 (2019) 371–375

Fig. 6. Fluorescence decay plot for BLC3 (upper panel) and BLC4 (lower panel) for emission wavelength of (a) λem = 365 nm and (b) λem = 425 nm, measured using
n-hexane and methanol as solvent. The instrumental response function (IRF) is also shown in each plot.

Table 1 organic light emitting diode, optoelectronic and sensing applications.


The Fluorescence decay life time (τ) obtained from least squares fitting of the To demonstrate the usefulness of the samples for sensor applications,
decay plots shown in Fig. 6. The errorbar in both cases is estimated to be we exposed all the samples (conc. ∼ 1.5 μM) in visible (white) light and
about ± 0.03 ns. UV light of wavelength ∼ 365 nm and ∼254 nm. The resulting optical
Sample (Solvent) Wavelength (λem τ1 ( ± 0.03) τ2 ( ± 0.03) χ2 images shown in Fig. 7 suggests that both the BLC samples in non-polar
nm) (ns) (ns) solvents have stronger green emission when exposed to 254 nm UV-
light, correspondingly, stronger blue emission when exposed to 365 nm
BLC3 (Hexane) 365 1.44 (28.12%) 6.35 (71.88%) 1.02
450 5.78 (52.88%) 13.6 (47.12%) 1.01
UV-light and stronger yellowish emission when exposed to visible white
BLC3 (Methanol) 365 1.36 (29.05%) 9.60 (70.95%) 1.5 light.
450 2.01 (15.69%) 9.76 (84.31%) 1.2
BLC4 (Hexane) 365 1.01 (24.78%) 6.05 (75.22%) 1.1 4. Conclusion
450 5.74 (51.55%) 14.3 (48.45%) 1.0
BLC4 (Methanol) 365 1.11 (26.19%) 8.97 (73.81%) 1.4
450 1.53 (14.42%) 10.6 (85.58%) 1.2 We have explored the photophysical characteristics of two bent core
liquid crystals C54H63NO9 (BLC3) and C60H75NO9 (BLC4). We con-
firmed that the nature (proticity) of the chosen solvent plays a very
Furthermore, considering the high PL intensity observed at important role in deciding the intramolecular and intermolecular hy-
λem = 365 nm for protic solvents and at λem = 450 nm for the aprotic drogen bond formation behavior of the BLCs. This inter-molecular/
solvents (Fig. 4), we may assign the shorter lifetime τ1 to the decay of intra-molecular hydrogen bond formation controls the overall excited
enol form of the molecule while that of τ2 to the keto form of the mo- state intramolecular proton transfer (ESIPT) emission behavior of the
lecule. The comparison of the lifetimes for BLC3 and BLC4 suggests that molecule. For protic solvents the BLCs show intense enol emission band
the length of the alkoxy chains at the end of the molecules have in- through the intermolecular bonding of the proton of the solvent with
significant role in the fluorescence behavior of the molecules. More- the Schiff-base, whereas for aprotic solvent the BLCs show intense keto
over, the longer lifetime τ2 obtained for both the BLCs suggests that the emission through the intramolecular hydrogen bonding. With increase
origin of the long tail in the emission spectra are due to vibrational in polarity of the protic solvents the enol emission band intensifies. Our
bands resulting from the bulky alkoxy chains attached to the ends of the results are useful for understanding and tuning the fluorescence beha-
BLC molecules. vior of bent core liquid crystals containing Schiff-base.
The estimated total quatntum yields of the BLC3 and BLC4 samples
(Table 2) show that both the molecules have very low quantum yields Conflicts of interest
in protic solvents and quite good quantum yields in aprotic solvents.
This behavior is similar to some other reported ESIPT molecules There are no conflicts of interest to declare.
[23,27], indicating that the molecules are potential candidates for
Acknowledgements
Table 2
The total quantum yield (Φs) of BLC3 and BLC4 in different solvents. The author S K Behera is grateful for the Dr. DS Kothari UGC fel-
lowship (CH/16-17/0063), New Delhi, India. The authors thank Mr.
Solvent ΦS (BLC3) ΦS (BLC4)
Rajeev Kumar (MRC, IISc Bangalore) for his help during initial test
Methanol 0.035 0.046 experiments.
Ethanol 0.085 0.099
2-Propanol 0.126 0.215
Appendix A. Supplementary data
Cyclohexane 0.173 0.397
n-Hexane 0.725 0.533
Supplementary data to this article can be found online at https://

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A.K. Satapathy, et al. Journal of Luminescence 210 (2019) 371–375

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