Journal of Luminescence 126 (2007) 728734

Excited state intramolecular proton transfer in amino

2-(2
0
-hydroxyphenyl)benzazole derivatives: Effects of the
solvent and the amino group position
Fabiano Severo Rodembusch

, Fernando Paulus Leusin,

Leandra Franciscato Campo, Valter Stefani

Universidade Federal do Rio Grande do Sul, Laboratorio de Novos Materiais Organicos, Av. Bento Gonc- alves,
9500. CP 15003 CEP 91501-970, Porto Alegre-RS, Brazil
1
Received 18 August 2006; received in revised form 7 November 2006; accepted 10 November 2006
Available online 18 December 2006
Abstract
The excited-state intramolecular proton transfer (ESIPT) mechanism in six amino 2-(2
0
-hydroxyphenyl)benzazole derivatives were
investigated in different solvents by means of UVvis absorption and steady-state uorescence. The amino benzazoles are uorescent in
the blue-orange region under UV radiation. Changes in the absorption, emission and excitation spectra were analyzed and correlated to
the position of the amino group and the solvent polarity. The equilibrium between the conformers in solution in the ground state,
conrmed by the solvatochromic effect, reects the dual uorescence emission presented by these dyes.
r 2006 Elsevier B.V. All rights reserved.
Keywords: Conformational equilibrium; Dual uorescence; ESIPT; Fluorescent dyes
1. Introduction
Compounds emitting uorescence through the excited-
state intramolecular proton transfer (ESIPT) mechanism
[16] have become a very attractive eld of research by
virtue of the widespread applications that can be envisaged
for these dyes, such as UV-light polymer stabilizers [7,8],
sensors [9] and laser dyes [10]. Particular interest
has recently been shown in a new class of ESIPT
amino benzazole derivatives, where applications such as
uorescent probes to label proteins and DNA [11] and new
polymeric materials [12,13] were also reported.
Although the solvent effect on the ESIPT mechanism
has been investigated experimentally [1416] and
theoretically [1721] in several structures, a discussion
concerning some amino 2-(2
0
-hydroxyphenyl)benzazole
derivatives (Scheme 1) is nowadays particularly interesting
since the amino group being strong electron donor in
the excited state, the uorescence spectrum of amino
derivatives are more sensitive to the solvent polarity than
the absorption spectrum [22]. These dyes have been used as
probe to discuss hydrophobichydrophilic environments
[23], for instance, in systems that use polymers for drug
delivery [22,24].
Usually in non-polar and aprotic solvents the normal
or enol-cis (E
I
) form is the most stable conformer of
these dyes in the ground state. This conformer on
excitation undergoes ESIPT to form the keto tautomer
(K
I
) (Scheme 2), which gives rise to an emission with large
stokes shift. Additional conformers are described and do
ARTICLE IN PRESS
www.elsevier.com/locate/jlumin
Scheme 1.
0022-2313/$ - see front matter r 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.jlumin.2006.11.007

Corresponding authors. Tel.: +55 51 33 16 62 85;

fax: +55 51 33 16 73 04.
E-mail addresses: rodembusch@iq.ufrgs.br (F.S. Rodembusch),
vstefani@iq.ufrgs.br (V. Stefani).
1
www.iq.ufrgs.br/lnmo.
not undergo ESIPT and are responsible for the short
wavelength normal emission [16]. In protic or polar
solvents, an enol-cis open conformer (E
II
) can exist [25].
In non-polar solvent enol-trans (E
III
) (when X O or S)
and enol-trans open (E
IV
) (when X NH) conformers
could also be stabilized [26,27]. In this way, this conforma-
tional equilibrium in solution has been observed experi-
mentally through the dual uorescence emission with an
emission at longer wavelengths ascribed to the excited keto
tautomer, and a blue-shifted one due to conformational
forms which presents a normal relaxation with Stokes shift
lower than 5834 cm
1
[21].
2. Materials and methods
The amino derivatives were prepared and puried as
already described in Ref. [12]. Spectroscopic grade solvents
(Merck) were used in uorescence emission and UVvis
absorption spectroscopy measurements. UVvis absorp-
tion spectra were recorded in a Varian Cary 50 spectro-
meter. Fluorescence emission and excitation spectra were
measured in a Hitachi spectrouorometer model F-4500.
Spectrum correction was performed to enable measuring of
a true spectrum by eliminating instrumental response such
as wavelength characteristics of the monochromator or
detector using rhodamine B as an internal standard
(quantum counter). All experiments were performed at
room temperature in a concentration range of 10
6
M.
3. Results and discussion
3.1. UVvis absorption characterization
Figs. 13 show the normalized UVvis absorption
spectra of these dyes in dichloromethane, acetonitrile and
ethanol. The relevant UVvis data are summarized in
Table 1.
An absorption band maxima (l
abs
max
) located around
331334 and 356372 nm, with molar extinction coefcient
values (e
max
) in agreement with pp* transitions, could
be observed in 4-AHBO and 5-AHBO, respectively.
The solvatochromic effect is higher in the 5-AHBO
(16 nm) if compared to 4-AHBO (3 nm). The absorption
maxima of the 4-AHBT (351357 nm) and the 5-AHBT
(368389 nm) present a higher dependence on the solvent
polarity (6 and 21 nm in 4-AHBT and 5-AHBT,
respectively), which can be explained by the better
electron delocalization allowed by the sulfur atom in
relation to the oxygen. The same photophysical behavior
was observed in the benzimidazole derivatives, with an
absorption maxima at around 329341 and 344362 nm in
4-AHBI and 5-HBI, respectively. The 5-AHBI presents
the higher dependence on the solvent polarity (18 nm)
in relation to the 4-AHBI (12 nm). The UVvis spectrum of
4-AHBI in ethanol exhibits a new peak shifted to the red
which is probably attributed to protonated AHBI in
the imidazolic nitrogen, as already observed in similar
heterocycles [28b]. The absence of this peak in the 5-AHBI
clearly indicates the eletronic effect of the amino group
position on the dye.
ARTICLE IN PRESS
Scheme 2.
280 300 320 340 360 380 400 420 440
O
N
HO
NH
2
N
o
r
m
a
l
i
z
e
d

a
b
s
o
r
b
a
n
c
e
Wavelength (nm)
O
N
NH
2
HO
Fig. 1. Normalized absorption spectra of the amino benzoxazoles 4-
AHBO and 5-AHBO in dichloromethane (solid line), acetonitrile (dash
line) and ethanol (dot line).
F.S. Rodembusch et al. / Journal of Luminescence 126 (2007) 728734 729
As already observed in similar heterocycles [2125], the
investigated benzazole derivatives present a conforma-
tional equilibrium in solution in the ground state,
conrmed by the solvatochromic effect observed in the
UVvis spectra. The increasing of the electronic delocaliza-
tion provided by the amino group in the benzazole
backbone is related to the red shift on the absorption
maxima, in relation to the 2-(2
0
-hydroxyphenyl)benzazole
analogs [28]. In addition, the dyes with the amino group in
the para position present the S
0
-S
1
transition bands red
shifted in relation to the meta position analogs, probably
due to a better electron delocalization [29]. This behavior
can be simply explained by the resonance structures of
these dyes.
The intense absorption bands observed at 280310 nm in
the para amino derivatives (5-HBO, 5-HBT and 5-HBI),
which are almost absent in the meta analogs also indicate
that the position of the amino group in the phenolic ring is
decisive for the photophysics of these dyes. The difference
of the absorption band intensities can be associated to a
difference of planarity of the dyes [30]. A non-planar
structure does not allow a more effective electronic
delocalization among the two p systems (phenolic and
benzoxazolic rings). In this way, the para amino derivatives
showed to be less planar than their meta analogs and the
intense bands at 280310 nm are related to the oxazole
chromophore [31]. The difference between the molecular
planarity of these dyes is conrmed taking the molar
extinction coefcient values into account. A less planar
structure usually presents a lower probability for the pp*
transition, as observed in the 5-amino benzazoles (Table 1).
3.2. Fluorescence characterization
Figs. 46 present the normalized uorescence emission
spectra of these dyes. The curves were obtained using the
absorption maxima as the excitation wavelengths. The
relevant data are summarized in Table 2.
The 4-AHBO presents in dichloromethane two uores-
cence emission bands (Fig. 4). A main band located at
ARTICLE IN PRESS
300 330 360 390 420 450 480
S
N
HO
NH
2
N
o
r
m
a
l
i
z
e
d

a
b
s
o
r
b
a
n
c
e
Wavelength (nm)
S
N
NH
2
HO
Fig. 2. Normalized absorption spectra of the amino benzothiazoles 4-
AHBT and 5-AHBT in dichloromethane (solid line), acetonitrile (dash
line) and ethanol (dot line).
280 300 320 340 360 380 400 420 440
N
N
HO
NH
2
H
N
o
r
m
a
l
i
z
e
d

a
b
s
o
r
b
a
n
c
e
Wavelength (nm)
N
N
NH
2
HO
H
Fig. 3. Normalized absorption spectra of the amino benzimidazoles 4-
AHBI and 5-AHBI in dichloromethane (solid line), acetonitrile (dash line)
and ethanol (dot line).
Table 1
Relevant UVvis data of the amino benzazole dyes in different solvents
l
abs
max
(nm)/e
max
10
4
(l mol
1
cm
1
)
4-AHBO 5-AHBO 4-AHBT 5-AHBT 4-AHBI 5-AHBI
Dichloromethane 331/2.85 369/0.95 351/4.55 384/1.31 329/4.26 361/1.47
Acetonitrile 334/1.58 372/0.86 357/4.21 389/1.31 330/2.57 362/0.60
Ethanol 333/5.30 356/1.83 353/5.32 368/0.84 341/3.08 344/0.31
F.S. Rodembusch et al. / Journal of Luminescence 126 (2007) 728734 730
467 nm ascribed to the ESIPT band and a blue-shifted one
located at 376 nm. Although the excited state process could
be responsible for these dual emission properties, we
believe that this photophysical behavior conrms the
conformational equilibrium in solution in the ground state.
The solvent shows to stabilize the enol-cis form in spite of
the E
II
and E
III
conformers in the ground state. In more
polar or hydrogen-bonding solvents, the emission band
intensities change. The blue-shifted band (377 nm) is more
intense and the ESIPT band (460 nm) appears with a very
small intensity. In ethanol and acetonitrile the conformers
responsible for the normal emission (E
II
and E
III
) seem to
be more stabilized than the E
I
conformer. Stokes shift
between 3344 and 3616 cm
1
were observed in these
conformers despite of the E
I
conformer (7962
8798 cm
1
), as expected when a phototautomerism takes
place in the excited state.
The 5-AHBO presents a similar photophysical behavior
in relation to the 4-AHBO. Two emission bands are
observed in dichloromethane. A main band at around
565 nm (ESIPT band) and a blue-shifted one located at
442 nm. In polar and protic solvents, the intensities of the
emission bands are also changed in relation to dichlor-
omethane. In acetonitrile, the main band (458 nm) is due to
the normal relaxation of the conformers and the ESIPT
band (581 nm) presents a very low intensity. In ethanol, the
main band is located at 492 nm. This band appears to
contain at the long-wavelength region, a considerable
contribution from the ESIPT band. To characterize this
photophysical behavior, the overall uorescence emission
curve was analyzed by deconvolution into partial curves
through the Origin
s
software using the Marquard algo-
rithm for multifunctional ts. In this way, the ESIPT band
is observed at 554 nm. For this dye a conformational
equilibrium between the E
I
and E
III
conformers are
expected to be present in all solvents.
ARTICLE IN PRESS
300 350 400 450 500 550 600 650 700 750
O
N
HO
NH
2 N
o
r
m
a
l
i
z
e
d

f
l
u
o
r
e
s
c
e
n
c
e
Wavelength (nm)
O
N
NH
2
HO
Fig. 4. Normalized uorescence spectra of the amino benzoxazoles 4-
AHBO and 5-AHBO in dichloromethane (solid line), acetonitrile (dash
line) and ethanol (dot line).
200 240 280 320 360 400

exc
= 470 nm

exc
= 378 nm
N
o
r
m
a
l
i
z
e
d

I
n
t
e
n
s
i
t
y
Wavelength (nm)

exc
= 467 nm

exc
= 376 nm
Fig. 5. Normalized uorescence excitation spectra of the 4-AHBO in
dichloromethane (left) and ethanol (right).
300 350 400 450 500 550 600 650 700 750 800
S
N
HO
NH
2
N
o
r
m
a
l
i
z
e
d

f
l
u
o
r
e
s
c
e
n
c
e
Wavelength (nm)
S
N
NH
2
HO
Fig. 6. Normalized uorescence spectra of the amino benzothiazole 4-
AHBT and 5-AHBT in dichloromethane (solid line), acetonitrile (dash
line) and ethanol (dot line).
F.S. Rodembusch et al. / Journal of Luminescence 126 (2007) 728734 731
In order to conrm the presence of conformers in
solution in the ground state, the uorescence excitation
spectra of the dyes were recorded at their enol and/or keto
uorescence emission wavelengths. It could be observed for
4-AHBO in dichloromethane from Fig. 5, that the
excitation at 376 nm (enol band) and 467 nm (ESIPT band)
give two distinct spectra, with an absorption maxima
located at 346 and 327 nm, respectively. In ethanol, the
same photophysical behavior is observed. The excitation at
378 nm (enol band) and 470 nm (ESIPT band) also give two
distinct spectra (absorption bands at 353 and 343 nm,
respectively). This indicates that the two uorescence bands
originate from at least two different conformers in the
ground state and the absorption spectra of this dye is a
mixture of these conformers in the ground state.
The 4-AHBT presents in dichloromethane a similar
photophysical behavior observed in the oxazole analogs.
The ESIPT band located at 500 nm and the blue-shifted
one located at 400 nm (Fig. 6). However, the intensity of
the blue-shifted band indicates that the conformers in
solution in the ground state (E
II
and E
III
) are more
stabilized in dichloromethane than their oxazole analogs.
In more polar solvents the intensities change. A main band
at 400 nm is observed and the ESIPT band is practically
undetected in ethanol (490 nm). In acetonitrile this band is
absent. In dichloromethane and ethanol the E
I
E
III
conformers are expected to be present in the ground state
and in acetonitrile the equilibrium is probably between the
E
II
and E
III
conformers.
The 5-AHBT presents in dichloromethane a dual
uorescence emission band, as already observed in the
4-AHBT and the oxazole analogs. The ESIPT band is
located at 606 nm and the blue-shifted band at 437 nm. In
more polar solvents, the 5-AHBT seems not to undergo the
ESIPT mechanism, since only one main band located at
477508 nm is observed. In this way, the 5-AHBT exists in
dichloromethane as a conformational equilibrium of the
E
I
E
III
forms in the ground state. In ethanol and
acetonitrile this equilibrium seems to be between the E
II
and E
III
conformers.
Fig. 7 presents the uorescence excitation spectra of the
4-AHBT. In dichloromethane, the spectra were recorded at
389 and 500 nm as excitation wavelengths to produce two
different spectra with absorption maxima located at 249
and 344 nm, respectively. The same behavior is observed in
ethanol. The excitation in the enol (396 nm) and ESIPT
(490 nm) bands also give two distinct spectra, as already
discussed for the benzoxazole analogs. This clearly
indicates the presence of the conformational equilibrium
in solution in the ground state. The absorption spectra of
4-AHBT is a mixture of the conformers in the ground state.
It is worth to mention that similar photophysical behavior
was observed for all amino derivatives presented in this
work.
Fig. 8 shows the 4-AHBI in all investigated solvents one
main uorescence emission band. These bands are located
at 424445 nm, between the normal and keto bands in
relation to the benzazole and benzothiazole analogs. The
solvatochromic effect and the single uorescence emission
band with a Stokes shift around 7000 cm
1
indicates that
this dye probably does not undergo ESIPT and the
observed uorescence emission is due to the E
II
E
IV
ARTICLE IN PRESS
Table 2
Relevant uorescent emission data of the amino benzoxazoles
Dye Solvent Normal Keto
l
em
max
(nm) Dl
ST
(cm
1
) l
em
max
(nm) Dl
ST
(cm
1
)
4-AHBO CH
2
Cl
2
376 3616 467 8798
Acetonitrile 376 3344 455 7962
Ethanol 378 3575 470 8753
5-AHBO CH
2
Cl
2
442 4476 565 9401
Acetonitrile 458 5048 581 9670
Ethanol 492 7765 554 10,039
4-AHBT CH
2
Cl
2
389 2783 500 8490
Acetonitrile 403 3197
Ethanol 396 3076 490 7920
5-AHBT CH
2
Cl
2
437 3158 606 9540
Acetonitrile 477 4743
Ethanol 508 7489
4-AHBI CH
2
Cl
2
445 7923
Acetonitrile 424 6718
Ethanol 432 6177
5-AHBI CH
2
Cl
2
414 3546 544 9318
Acetonitrile 423 3984 556 9639
Ethanol 479 8193 542 10,619
F.S. Rodembusch et al. / Journal of Luminescence 126 (2007) 728734 732
conformers. In addition, this particular photophysical
behavior is probably due to the E
IV
conformer, which
can only exist in the benzimidazoles.
The 5-AHBI presents in dichloromethane and
acetonitrile a dual uorescence, with the corresponding
ESIPT band located at around 550 nm and the normal
relaxation at 415 nm. In these solvents, the conformational
equilibrium in the ground state is expected to be between
the E
I
and E
IV
conformers. In ethanol, a behavior similar
to the oxazole analog was observed. The band ascribed to
the normal relaxation located at 479 nm and the ESIPT
band located at 542 nm, obtained in the long-wavelength
region from deconvolution into partial curves. In this way
the conformational equilibrium is ascribed to be between
the E
I
and E
IV
.
4. Conclusions
Results show that the positions of the amino group in
the phenyl ring and the solvent polarity play a fundamental
role in the photophysics pathways of the dyes. The
equilibrium between the conformers in solution in the
ground state, conrmed by the solvatochromic effect,
reects the dual uorescence emission presented by these
dyes. The emission at long wavelengths is ascribed to the
ESIPT band and is due to an excited keto tautomer. In
addition, the blue-shifted band is due to conformational
forms, which are stabilized in solution and present a
normal relaxation.
The UVvis spectra of the dyes also shows that the
position of the amino group in these dyes is decisive in the
conformational equilibrium in the ground state by: (i)
increasing the electronic delocalization, observed experi-
mentally by the red shift bands of the derivatives with the
amino group in the para position in relation to the meta
analogs and (ii) changing the expected planar structure of
these dyes, conrmed by the difference of intensities of the
absorption band at 280300 nm.
Acknowledgments
We are grateful for nancial support and/or scholarships
from the Brazilian agencies CNPq, FAPERGS and CAPES.
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exc
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Wavelength (nm)
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