Journal of Luminescence 81 (1999) 61—70

Photoinduced proton transfer in 3-methyl-6-hydroxy-m-phthalic

acid
Ranjan Das , Sivaprasad Mitra
, Dipanwita Guha, Samaresh Mukherjee*
Department of Chemistry, J.K. College, Purulia, W. Bengal, India

Department of Chemistry, School of Science, Kwamsei Gakuin University, Nishinomiya 662, Japan
 Department of Physical Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700032, India
Received 25 February 1998; received in revised form 13 July 1998; accepted 27 July 1998

Abstract

The ground and excited state photophysics of 3-methyl-6-hydroxy-m-phthalic acid (HmPA) has been studied in
homogeneous solvents by steady state, nanosecond transient emission spectroscopy and semiemperical AM1 calcu-
lations. HmPA shows variations in steady-state spectra depending on the solvent characteristics. A large Stokes-shifted
emission in the nonpolar solvent (&9500 cm\,)j "325 nm and j"470 nm) indicates that on UV excitation the keto
form of HmPA undergoes intramolecular proton transfer (ESIPT) leading to tautomerization in the singlet excited state.
This particular emission (type-I emission) attributed to the enol tautomer of HmPA, is characterized by a very low
emission quantum yield (
&0.08). But in strong hydrogen bonding solvents like ethanol and water another relatively
stronger (type-II emission,
&0.3—0.5 depending on the solvent) but small Stokes-shifted fluorescence (j "360 nm and
j"410—430 nm) is observed. The fluorescence maximum for this particular type of emission depends on the static
polarity of the solvent (j varies from 410 nm in ethanol to 430 nm in water). In the ground state, very rapid
deprotonation from the carboxylic acid groups occurs in the hydrogen bonding solvent medium resulting in dicar-
boxylate anion of HmPA. The ground state closed conformer (keto form) of this dicarboxylate anion of HmPA
undergoes thermodynamically favourable intramolecular proton transfer in the ground state (GSIPT) leading to the
formation of proton transferred form (enol tautomer). All the experimental findings were explained with the theoretical
results obtained from CNDO/S-CI calculations.  1999 Elsevier Science B.V. All rights reserved.

Keywords: Proton transfer; 3-methyl-6-hydroxy-m-phthalic acid; Solvent effect

1. Introduction energy [2], processes related to the absorption of

Molecules, undergoing excited state intra-
molecular proton transfer (ESIPT) reaction, are
important in connection with promotion of laser
action [1], conversion of solar energy into electrical
* Corresponding author. Tel.: #91 33 473 5374; Fax: #91
33 473 2805; e-mail: pcsm@mahendra.iacs.res.in.
ultraviolet light by chemical and biochemical sys-
tems [3,4] and solvation dynamics [5]. Due to its
wide spread applications in science and technology,
ESIPT reaction has attracted a number of experi-
mental and theoretical scientists [6].
Although proton transfer reaction of salicylic
acid (SA) was known at least four decades ago [7],
studies on this system are not very common. This
is due to the fact that o-hydroxy carboxylic

0022-2313/99/$ — see front matter  1999 Elsevier Science B.V. All rights reserved.
PII: S 0 0 2 2 - 2 3 1 3 ( 9 8 ) 0 0 0 5 0 - 7
62 R. Das et al. / Journal of Luminescence 81 (1999) 61—70
compounds like SA dimerize readily on increasing
concentration and get ionized in polar solvents, so
that studies of these systems were mainly confined
to the derivatives of SA such as methyl salicylate
(MS) [8]. But as the experimental techniques have
advanced considerably, it has now become possible
to use these systems as a probe for ESIPT [9,10].
Again SA and its derivatives are used as charge
control additives in dry xerographic toner at low
concentrations to control the charging character-
istics of toner [11—13]. The technological relevance
of ESIPT necessitates a further systematic study on
the mechanism of this process.
The results of the fluorescence properties of SA
and its derivatives have created a long standing
debate but the essential features obtained so far can
be summarized as follows. Electronic excitation
causes the phenolic oxygen to become more acidic
which causes ESIPT to occur. Two types of emis-
sions are observed. Type-I emission has very low
quantum yield, largely Stokes shifted from the ab-
sorption band observed in the hydrocarbon and
nonpolar solvents whereas type-II emission ob-
served only in highly polar, protic and aprotic
solvents are of relatively larger quantum yield (
). with an SP-70 nanosecond spectrometer (Applied

The origin of the two fluorescence bands is not
unambiguous. Pant et al. [9] proposed that the
strongly Stokes-shifted band is due to the rapid
proton transfer in the excited state to give rise to
tautomer whereas the normal form emits to give
the “blue” band. But Law et al. [10] showed for
) and all other experimental details
3,5-t-butyl salicylic acid (t-BSA) that the car-
boxylate anion is the only precursor to tautomeriz-
ation. They also pointed out that a clear view for
the mechanism of proton transfer (PT) can be
achieved only on the basis of reasonable theoretical
calculations.
For the last few years, we had been engaged in
studying the dynamic aspects of PT reaction in
homogeneous and microheterogeneous medium
[14—16]. The dynamics of PT in 4-methyl-2,6-difor-
myl phenol (MFOH) and its derivatives have been
discussed in the light of experimental results and
theoretical calculations [17,18]. In this present pa-
per we wish to report our findings on 3-methyl-6-
hydroxy m-phthalic acid (HmPA) with a special
emphasis on the elucidation of the mechanism of
PT by fluorescence spectroscopy and semiemperi-
cal AM1 and CNDO/S-CI calculations. We have
also discussed the photophysical properties of
HmPA in comparison to the findings of Law et al.
for t-BSA. To clarify the proposed mechanism fur-
ther, some complimentary studies have been car-
ried out with isophthalic acid (IPHA).
2. Experimental
Like 4-methyl-2,6-diformylphenol (MFOH) and
4-methyl-2,6-diacetylphenol (MAOH), 3-methyl-6-
hydroxy-m-phthalic acid (HmPA) was prepared by
the department of inorganic chemistry of this insti-
tute in a similar way to that reported earlier
[19,20]. Isophthalic acid (IPHA) was received from
Merck (Schuchardt) and used as such. The solvents
ethanol, cyclohexane, n-hexane and 1,4-dioxane
were of spec-grade and used as received. Acetic acid
used was of A.R. grade. Triply distilled water was
used throughout. Absorption, emission and excita-
tion spectra were recorded on a JASCO 7850 and
a Perkin-Elmer MPF 44B spectrophotometer. The
transient fluorescence lifetime (q ) was measured

Photophysics Ltd., UK) using a pulsed nitrogen
lamp based on the time correlated single-
photon-counting technique. Concentration of all
the compounds were maintained at 4 to
8;10\ mol dm\. The relative fluoresence quan-
tum yields (

were the same as reported earlier [19].
3. Results
3.1. Steady state spectra
Fig. 1a shows the electronic absorption spectra
of dilute HmPA solution (&10\ mol dm\) in
different solvents. A single absorption peak with
a maximum at 325 nm is obtained in nonpolar
solvents such as cyclohexane, n-hexane and 1,4-
dioxane whereas in water another shoulder appear
at 360 nm region in addition to the 325 nm band.
Electronic spectra of HmPA in ethanol show only
a single band at 360 nm. The fluorescence emission
 R. Das et al. / Journal of Luminescence 81 (1999) 61—70 63

Fig. 1. Absorption (a) and emission (b) spectra of HmPA in 1,4-dioxane (1), water (2) and ethanol (3). [HmPA]"4.3;10\ (M) in each
case. Absorption, emission and excitation spectra of IPHA (c): Absorption in ethanol (i); emission (ii) in ethanol (1) and methylcyc-
lohexane (2); excitation in methylcyclohexane (3). [IPHA]"3.8;10\ (M) in each case.

spectra of HmPA (Fig. 1b) in cyclohexane, n-
hexane and 1,4-dioxane appear at 470 nm with
a large Stokes shift (&9500 cm\ from peak to
peak) relative to the absorption band (Fig. 1a). The
excitation spectra of this band match exactly with
the absorption spectra in all the cases. The emission
spectra of HmPA (Fig. 1b) in ethanol shows only
one peak with a maximum at 410 nm and the
peak-to-peak Stokes shift in these cases are rela-
tively small (&3400 cm\). Monitoring the emis-
sion at this wavelength, the excitation band appears
at 360 nm which is exactly similar to that of the
absorption band in ethanol. The mirror image rela-
tionship of the fluorescence spectra with the
absorption band indicates that the fluorescence
emission arises directly from the species absorbed
at 360 nm. The 360 nm absorption in ethanol is due
to the solvent assisted open conformer of HmPA.
64 R. Das et al. / Journal of Luminescence 81 (1999) 61—70

The emission spectra of water shows a maximum at
430 nm and the corresponding excitation spectra
displays a band at 360 nm.
We have found no change in spectral properties
of HmPA with variation in solution concentration
"0.33) which is
up to &10\ mol dm\. The solutions obey Beer’s
law up to this concentration level and it can be
inferred that HmPA does not undergo dimerization
on increasing the concentration. Even the solid
sample of HmPA shows a single large Stokes-shif-
ted emission band at 470 nm.
band at 470 nm decreases in intensity, finally disap-
pears and a new band at 410 nm is observed. Addi-
tion of base to the solution of HmPA in ethanol
causes a large increase in fluorescence intensity and
410 nm band shifted to 430 nm (

exactly similar to that observed in water, whereas
the reverse trend is observed by the addition of acid

3.2. Effects of acid and base on the steady state

spectral properties

Fig. 2 shows the effect of addition of a base like

triethyl amine (TEA) on the spectral properties of
HmPA in 1,4-dioxane. It is found that with the
increasing concentration of TEA the fluorescence

Fig. 3. Absorption (a) and emission (b) spectra of HmPA in

ethanol, in presence of dilute acetic acid [ACOH].
Fig. 2. Emission spectra of HmPA in 1,4-dioxane in presence of [ACOH]/mol dm\"0 (0), 1.4;10\ (1), 2.8;10\ (2),
TEA. [TEA]/mol dm\"0 (0), 2.4;10\ (1), 7.6;10\ (2), 4.2;10\ (3), 5.6;10\ (4), 7.0;10\ (5), 8.4;10\ (6),
1.3;10\ (3). 9.8;10\ (7).
 R. Das et al. / Journal of Luminescence 81 (1999) 61—70
in these solutions. The 410 nm band can be as-
signed as due to the intermolecularly hydrogen
bonded complex formed by the interaction with
solution medium. The addition of dilute acetic acid
in ethanol, causes a decrease in absorbance of
360 nm band with a simultaneous appearance of
a second absorption band at 325 nm (Fig. 3a). Also,
the steady state fluorescence spectra show some
interesting changes in the presence of dilute acid.
Increasing the concentration of dilute acetic acid
induces a decrease in the fluorescence emission at
410 nm and enhances appearance of a new emis-
sion band at 470 nm (Fig. 3b). By the addition of
aqueous alkali, in water solution of HmPA, the
intensity of 430 nm band increases without any
change in position. Accordingly the 430 nm emis-
sion band can safely be assigned as due to the anion
of HmPA. But the addition of acid has no effect on
the spectra of HmPA in hydrocarbon and nonpolar
solvents.
Fig. 4. Absorption (a) and emission (b) spectra of HmPA in 1,4-dioxane/water mixture. Vol% of water in (a): 0 (0), 33 (1), 66 (2), 100 (3).
Vol% of water in (b): 0 (0), 50 (1), 66 (2), 100 (3).
65
3.3. Spectral studies in mixed solvents
Addition of water as a cosolvent in pure 1,4-
dioxane solution of HmPA (keeping the solute con-
centration fixed always) results in the formation of
360 nm band in the electronic spectra in addition to
the 325 nm band (Fig. 4a). The 470 nm emission
band in 100% (v/v) 1,4-dioxane undergoes a blue
shift to 410 nm in 50% (v/v) dioxane-water mixture.
Again, with an increase in the water content of the
solvent mixture the emission band at 410 nm shifts
to 430 nm (Fig. 4b).
3.4. Decay behaviour of HmPA fluorescence
The decay behaviour of HmPA fluorescence
obeys single exponential kinetics in all the solvents.
In 1,4-dioxane the 470 nm emission decays in
a single exponent with a lifetime (q ) value of 3.6 ns.

However, the fluorescence at 410 and 430 nm in
66 R. Das et al. / Journal of Luminescence 81 (1999) 61—70

ethanol and water decays with lifetime (q ) values of

4.5 and 4.8 ns, respectively. However, the behaviour
of HmPA fluorescence in 1 : 1 (v/v) dioxane—water
mixture shows biexponential kinetics when
monitored at 470 and 410 nm. The relative integ-
rated fluorescence intensities for the 470 and
410 nm components are 35% and 65%, respectively.
4. Discussions
The 325 nm absorption band in HmPA is at-
tributed to the intramolecularly hydrogen bonded
closed conformer (I, Fig. 5) of HmPA. This is in
analogy with our previous observation made on
MFOH in n-hexane and cyclohexane [14]. In
ethanol and water, a second absorption band at
360 nm region is observed in addition to the
325 nm band. The measured pH of a solution of
HmPA in ethanol and water are 8.3 and 5.0, respec-
tively, which suggest that in these solvents HmPA
undergoes rapid intermolecular interaction with
solvent medium and results in the formation of
hydrogen bonded complex with solvent molecules.
This leads us to the fact that the second absorption
band or the shoulder at 360 nm region in ethanol
and water can be attributed to the intermolecularly
hydrogen bonded open conformer. The emission

Fig. 5. Schematic representation of different conformers of HmPA and IPHA: HmPA closed conformer (I), HmPA anion (II), hydrogen
bonded complex of HmPA (III) where B is the base added to the solvent medium, IPHA (IV), HmPA tautomer (V) and anion of HmPA
tautomer (VI)*.
 R. Das et al. / Journal of Luminescence 81 (1999) 61—70
spectra in water both in the presence and absence of
base appeared at 430 nm indicating the presence of
anion of HmPA. In ethanol, on the other hand,
a promoter base is necessary for the formation of
anion. The 410 nm band in ethanol,or in 1,4-diox-
ane in presence of TEA, is attributed to hydrogen
bonded complex formed due to solute—solvent in-
teraction even in the excited state. Thus complete
transfer of proton even in the excited state is pos-
sible only in water. On the other hand, the presence
of a strong base is necessary for the HmPA anion
formation in ethanol.
In this connection, our observations are found to
be quite different from that of Law et al. for 3,5-di-
tert-butyl salicylic acid (t-BSA). t-BSA exhibits dif-
ferent absorption bands at 320—324 nm in nonpolar
solvents and this absorption band suffers a hy-
psochromic shift in aprotic solvents as solvent po-
larity increases. In alcohols, the j is found to

correlate primarily to the structure of the solvent
molecule rather than the solvent polarity. They
found that j tends to shift to longer wavelengths

as the steric hindrance around the OH group in-
creases, and they suggest that the blue shifted
absorption maxima of t-BSA is due to the forma-
tion of solvent—solute complex, presumably
through the hydrogen bonding between the OH
group in the alcohol and the salicylic acid group in
t-BSA. However, we have failed to observe any shift
in j in going from ethanol to hexanol.

The large Stokes-shifted emission of HmPA in
nonpolar solvents at 470 nm is analogous to the
spectral features observed for MFOH in nonpolar
solvents which suggests that an ultrafast intra-
molecular proton transfer (ESIPT) across the
intramolecular hydrogen bond between phenolic
and carboxylic carbonyl groups has taken place
[14]. It has been established that if a proton dona-
ting hydroxyl group is hydrogen bonded in the
ground state, the excited state intramolecular pro-
ton transfer (ESIPT) is usually evidenced by a large
Stokes-shifted emission in nonpolar solvents, as-
suming proton transfer occurs during the lifetime of
the excited molecules [21]. In the case of HmPA
the large Stokes-shifted emission (&9500 cm\)
can safely be assigned as due to the ESIPT in
nonpolar solvents as is observed in the case of
MFOH [14]. The ESIPT has been shown to occur
67
rapidly as long as the intramolecular hydrogen
bond remains unperturbed. In ethanol ESIPT
cannot occur due to the stronger interaction
with solvent molecules and rupture of intramolecu-
lar bond. However, when the proton of phenolic
group of HmPA is replaced by a methyl group in
methyl 2-methoxy benzoate (MOMB) (III, Fig. 5),
a structurally related chromophore of HmPA,
a small Stokes-shifted emission from locally ex-
cited state is observed around 350 nm. Also, for
isophthalic acid (IPHA) (IV, Figs. 5 and 1c) where
the phenolic group is absent the absorption and
emission bands appear at about 290 and 340 nm,
respectively. All these observations clearly indicate
that the anomalous large Stokes-shifted emission
of HmPA at 470 nm in nonpolar solvents arises
due to the enol tautomer (V, Fig. 5) formed
due to the ESIPT of the closed conformer (keto
form) (I, Fig. 5) of HmPA. To explain the steady-
state results we propose the following model
(Scheme 1) for the photophysics of HmPA in vari-
ous solvents.
We have observed the second fluorescence band
for HmPA at 410—430 nm (type-II) emission which
is intense and largely blue shifted relative to the
type-I emission (470 nm).
Type-II emission seems to originate from photo-
excitation of the hydrogen bonded complex (III,
Fig. 5) or a form derived from it as described in our
model (Scheme 1). This is further substantiated
from acid/base effect and mixed solvent experi-
ments. On addition of dilute TEA to a solution of
HmPA in pure dioxane, a new band develops at
360 nm in the absorption spectrum, at the expense
of 325 nm band. Also, the tautomer band at 470 nm
due to ESIPT, decreases in intensity and the band
shifts to 410 nm. Following further addition of
TEA, the 410 nm band increases in intensity. The
addition of dilute acetic acid to a solution of HmPA
in ethanol, decreases the absorbance of 360 nm
band and another band appears at 325 nm
(Fig. 3a). In the emission spectrum, the 410 nm
band in ethanol decreases with increasing acetic
acid concentration (Fig. 3b) with the appearance of
another band at 470 nm. However, in dioxane, ad-
dition of dilute acetic acid does not affect the
absorption and emission spectrum. All these obser-
vations can be explained according to our model.
68 R. Das et al. / Journal of Luminescence 81 (1999) 61—70
Scheme 1. ESIPT and GSIPT in H PA.
On addition of TEA to a HmPA solution of
1,4-dioxane, TEA interacts with CO H groups to

form hydrogen bonded complex of HmPA with
a consequent decrease in the 325 nm absorption
band. Due to this reason the emission band at
410 nm in ethanol that originated due to hydrogen
bonded complex of HmPA or a form derived
from it, increases in intensity, followed by a
decrease in intensity of the 470 nm band, origin-
ating from photoexcitation of neutral closed
conformer of HmPA. On addition of acid, the
hydrogen bond of HmPA gets ruptured, resulting
in the formation of neutral closed conformer of
HmPA. Due to this reason, the ground state
population of neutral HmPA increases significantly
followed by a decrease in population of HmPA
complex. As a result, the 410 nm band decreases
in intensity and the 470 nm band, attributed to
ESIPT phototautomer, develops and increases in
intensity.
In case of mixed solvent experiments, with in-
creasing vol% of water as a cosolvent in binary
solvent mixture of dioxane—water, a second absorp-
tion band at 360 nm develops (Fig. 4a). In the emis-
sion spectrum the 470 nm band due to enol
tautomer shifts to 410 nm at 50% (v/v) water and
increases in intensity by addition of water up to
66% (v/v). In 100% water (v/v), the 410 nm band
again shifts to the red at 430 nm. This can be
explained by assuming that with increasing vol% of
water as a cosolvent, the interaction capability of
the solvent media increases with a subsequent
formation of dicarboxylate of HmPA. This also
results in a blue shift of emission band of tautomer.
As the ground state population of HmPA anion
increases with increasing vol% of water,
the 410 nm band increases in intensity and on
further addition of water, this band shifts to
430 nm due to dielectric relaxation and formation
of anion.
Thus, it appears that in ethanol (in presence of
base) and water deprotonation of dicarboxylic acid
groups occur in HmPA, resulting in the dicar-
boxylate anion of HmPA. Our theoretical
calculations for CNDO and S—CI show that the
dicarboxylate anionic form of HmPA undergoes
thermodynamically favourable rapid ground
state intramolecular proton transfer (GSIPT),
(*Ek ¹) (*E"2.76 kCal/mol, from semiemperi-
cal AM1 calculations, R¹+0.59 kCal/mol) to
form enol tautomer of ground state dicarboxylate.
The ESIPT reaction is characterized by a double
well potential energy surface having the reactant in
one side and the reaction product (phototautomer)
in the other. The barrier height between the station-
ary points determines the course of ESIPT reaction
 R. Das et al. / Journal of Luminescence 81 (1999) 61—70
i.e. whether this reaction proceeds via proton tun-
nelling or as a part of intramolecular vibrational
relaxation in a barrierless adiabetic potential. How-
ever, the energy barrier for this GSIPT process is
found to be +3.1 kCal/mol as revealed by the
semiemperical AM1 calculations. This observation
suggests that the reaction may proceed via proton
tunnelling. Following the photoexcitation of this
enol form of ground state, a locally excited emission
occurs at 410 nm in ethanol which shifts to 430 nm
in water due to dielectric relaxation and formation
of anion. In nonpolar, noninteracting solvents
ESIPT of the keto form of HmPA occurs resulting
in the enol tautomer.
The results of the time-resolved emission experi-
ments also support our arguments. In 1,4-dioxane
the 470 nm emission decays monoexponentially
with a time constant (q ) of 3.6 ns. However, the

410 nm emission in ethanol and 430 nm emission in
water decays monoexponentially with time con-
stants (q ) of 4.6—4.8 ns. This observation suggests

that the 470, 430 and 410 nm emissions in 1,4-
dioxane, water and ethanol, respectively, are due to
different conformers of HmPA.
The mixed solvent experiment for 1 : 1 (v/v) diox-
ane—water mixture suggests biexponential decay
kinetics when monitored at 470 or 410 nm. The
relative integrated intensity for the fast decaying
component (q "3.5 ns) and slow decaying com-

ponent (q "5.2 ns) are found to be 34% and 66%,

respectively, which suggests coexistence of two ex-
cited state species and two ground state species in
dioxane—water mixture.
However, the more intense type-II emission for
HmPA in polar, aprotic and protic solvents is at-
tributed to be originated from photoexcitation of
ground state enol tautomer of dicarboxylate anion
of HmPA, which results from thermodynamically
favourable ground state intramolecular proton
transfer (GSIPT) of intramolecularly hydrogen
bonded closed conformer of dicarboxylate anion of
HmPA. These findings are contrary to observa-
tions of Law et al. in respect of t-BSA, where they
suggested that the primary photochemical reaction
of excited t-BSA is to form deprotonated anion of
t-BSA even in nonpolar solvents, and the type-II
emission in polar, protic solvents is due to ESIPT
of solute—solvent complex.
69
5. Conclusions
The solvent effect, acid—base effect, structural
effect experiments and semiemperical AM1 calcu-
lations suggest that type-I emission of HmPA oc-
curs due to ESIPT of intramolecularly hydrogen
bonded closed conformer or keto form of HmPA.
However, the more intense type-II emission of
HmPA in polar, aprotic and protic solvents is at-
tributed to originate from photoexcitation of
ground state enol tautomer of HmPA, which re-
sults from thermodynamically favourable rapid
ground state intramolecular proton transfer
(GSIPT) of intramolecularly hydrogen bonded
closed conformer of HmPA.These findings are con-
trary to the observations of Law et al. as in case of
t-BSA, they suggested the primary photochemical
reaction of excited t-BSA is to form deprotonated
anion even in nonpolar solvents, and the type-II
emission in polar, protic solvents is due to ESIPT
of solute—solvent complex.
Acknowledgements
RD and SM are grateful to CSIR for providing
them with Research Fellowships. DG wishes to
thank CSIR for providing her with Junior Research
Fellowship.
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