Synthesis, characterization, spectroscopic properties, theoretical calculation, and antimicrobial activity of new aryldisulfonamides

Article abstract of DOI:10.1016/j.molstruc.2011.02.024

New aryldisulfonamides were synthesized and characterized by FTIR, ¹H NMR, ¹³C NMR, HETCOR, COSY, LC-MS and elemental analysis techniques. The compounds gave intense emissions, where λ_max = 405, 379 and 402 nm, upon irradi

Full text of DOI:10.1016/j.molstruc.2011.02.024

Journal of Molecular Structure 992 (2011) 27–32
Contents lists available at ScienceDirect
Journal of Molecular Structure
journal homepage: www.elsevier.com/locate/molstruc
Synthesis, characterization, spectroscopic properties, theoretical calculation,
and antimicrobial activity of new aryldisulfonamides
a,
⇑
b
c
d
Saliha Alyar , Hüseyin Zengin , Neslihan Özbek , Nurcan Karacan
a
Department of Chemistry, Science Faculty, Çankırı Karatekin University, 18100 Çankırı, Turkey
Department of Chemistry, Science and Art Faculty, Gaziantep University, 27310 Gaziantep, Turkey
Department of Primary Education, Faculty of Education, Ahi Evran University, 40100 Kırsehir, Turkey
Department of Chemistry, Science and Art Faculty, Gazi University, 06500 Ankara, Turkey
b
c
d
a r t i c l e i n f o
a b s t r a c t
New aryldisulfonamides were synthesized and characterized by FTIR, 1H NMR, 13C NMR, HETCOR, COSY,
LC-MS and elemental analysis techniques. The compounds gave intense emissions, where kmax = 405, 379
and 402 nm, upon irradiation by Ultra-Violet light. The photoluminescence quantum yields and long
excited-state lifetimes of the compounds were calculated and were found to have photoluminescence
quantum yields 39 ± 1.8%, 45 ± 2.2% and 34 ± 1.4% and long excited-state lifetimes of 3.65 ± 0.16,
Article history:
Received 26 November 2010
Received in revised form 10 February 2011
Accepted 11 February 2011
Available online 17 February 2011
4
.17 ± 0.20 and 3.15 ± 0.12 ns, respectively. The photoluminescence intensities and quantum yields of
Keywords:
Disulfonamides
Photoluminescence
Antimicrobial activity
TD-DFT/B3LYP calculations
ZINDO/S calculations
compounds varied with the position of substituent on the ring and the chain length between aromatic
rings. These novel compounds may be of interest as organic emitting materials for electroluminescent
devices. The visible absorption maxima were calculated using time-depended density-functional theory
(TD-DFT) and Zerner’s intermediate neglect of differential overlap/spectroscopic (ZINDO/S) method in the
gas phase. Further, the compounds were evaluated for in vitro antimicrobial activity against various
microorganisms by microdilution and disk diffusion methods.
Ó 2011 Elsevier B.V. All rights reserved.
1
. Introduction
Sulfonamides were the first effective chemotherapeutic agents
have also been developed as hole transport layers in organic elec-
troluminescent research [15,16]. The synthesis and fluorescence of
N-substituted 1- and 2-aminopyrenes have been studied and their
absorption and fluorescence spectra as well as fluorescence quan-
tum yields in different solvents were measured and reported [17].
Their study revealed that the fluorescence quantum yield was
dependent on both the structure and solvent polarity. Fluorescent
vic-dioxime-type ligand and its mono- and dinuclear complexes
have been studied [18]. Thus it was noted that the fluorescence
spectra of the probe showed a clear shift in excitation wavelength
maxima upon metal binding indicating its potential use as ratio-
metric metal indicator.
In our previous work aliphatic/aromatic disulfonamides and
methanesulfonic acid hydrazides/hydrazones were synthesized
and tested for antimicrobial and cytotoxic activity [19–26]. Studies
herein present the synthesis and characterization of a series of no-
vel disulfonamide derivatives (1–3) and are shown in Fig. 1. The
optical properties of these compounds in solution were also exam-
ined. The disulfonamides were found to exhibit photolumines-
cence, emitting an intense light upon UV irradiation. Further
absorption spectra were obtained by semi-empirical ZINDO/S and
TD-DFT methods and were compared with experimental data.
Antibacterial activities of the synthesized compounds against
Gram-positive bacteria (Staphylococcus aureus ATCC 25953, Bacillus
employed systematically for the prevention and the cure of bacte-
rial infections in humans and other animal systems [1,2]. After the
introduction of the penicillin and other antibiotics the popularity
of sulfonamides decreased. However they are still used as sulfa
drugs such as sulfadiazine, sulfathiazole, sulfamerazine in certain
therapeutic fields especially in the case of ophthalmic infections
and for urinary and gastrointestinal infections [3,4]. Multidrug
resistance (MDR) remains as a significant problem for microbial
infection treatments [5–8]. Additionally the threat of bioterrorism
using agents such as weaponized Bacillus anthracis and Yersinia
pestis highlight the need for continuing research in infectious dis-
eases and the search for new therapeutic agents [9]. Organic light
emitting devices represent an important field of research and has
attracted a great deal of attention over recent years [10–12]. For
example, organic polymers which exhibit strong luminescence at
low driving voltages and in particular those that emit in the blue
region are of great interest for flat panel display applications
[
13,14]. Numerous aromatic amines and polymeric arylamines
⇑
Corresponding author. Tel.: +90 376 2181123; fax: +90 376 2181031.
E-mail address: saliha@karatekin.edu.tr (S. Alyar).
0
022-2860/$ - see front matter Ó 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.molstruc.2011.02.024

2
8
S. Alyar et al. / Journal of Molecular Structure 992 (2011) 27–32
Fig. 1. The chemical structures and labels of atoms for disulfonamides (1–3).
cereus ATCC 6633 and Bacillus megaterium RSKK 5117) and Gram-
negative bacteria (Escherichia coli ATCC 11230 and Salmonella
enterititis ATCC 13076) were evaluated by disk diffusion and micro-
dilution methods.
chloride 3.85 mL (0.04 mol) a white solid was obtained. The prod-
uct was filtered and recrystallized from a ethanol/n-hexane (4/1)
mixture and was dried in vacuuo and stored under ethanol vapor:
ꢀ1
Yield 78%; mp 183–184 °C; IR (KBr) cm : 3281
t
(NH), 1452 d(NH)
); Anal. Calcd. for
24 2 4 2
H N O S : C, 54.52; H, 6.10; N, 7.06; S, 16.17, Found: C,
,
2
C
5
3 2 2
979 t(CH ), 1317 tasym.(SO ), 1169 tsym.(SO
18
2
. Experimental procedure
4.47; H, 6.00; N, 7.05; S, 16.10.
2.1. Materials and instrumentation
0
2
.2.2. Synthesis of N,N -butanediyl-bis-3-methylbenzenesulfonamide
The elemental analyses (C, H, N and S) were performed on a
(
2)
LECO CHNS 9320 type elemental analyzer. The IR spectra (4000–
ꢀ1
Using the general procedure described above from 4.06 mL
0.08 mol) 1,4-diamino butane and 3-methylbenzenesulphonyl
chloride 3.85 mL (0.04 mol) a white solid was obtained. The prod-
uct was filtered and recrystallized from a ethanol/n-hexane (4/1)
mixture and was dried in vacuo and stored under ethanol vapor:
Yield 80%; mp 183–184 °C; IR (KBr) cm : 3294
d(NH) 2947 (CH ), 1323 ), 1169
for C18 : C, 54.52; H, 6.10; N, 7.06; S, 16.17, Found: C,
4.51; H, 6.00; N, 7.00; S, 15.99.
4
00 cm ) were recorded on a Mattson 1000 FT-IR Spectrophotom-
(
eter with samples prepared as KBr pellets. NMR spectra were re-
corded on a Bruker-Spectrospin Avance DPX-400 Ultra–Shield
400 MHz) using DMSO as the solvent with TMS as the internal
standard. LC/MS-APCl was recorded on an AGILENT 1100 Spec-
trometer. The melting points were measured using an Opti Melt
apparatus. TLC was conducted on 0.25 mm silica gel plates (60F
(
ꢀ1
t
(NH), 1439
,
t
3
t
asym.(SO
2
tsym.(SO ); Anal. Calcd.
2
24 2 4 2
H N O S
2
54, Merck). All solvents were purchased from Merck and reagents
5
were obtained from Aldrich Chem. Co. (ACS grade) and used as re-
ceived. The single-photon fluorescence spectra of the compounds
were collected on a PerkinElmer LS55 Luminescence Spectrometer.
All the samples were prepared in spectrophotometric grade tetra-
hydrofuran (THF) and analyzed in a 1 cm optical path quartz cuv-
ette. The solution concentration of the compounds in THF was
0
2
.2.3. Synthesis of N,N -pentanediyl-bis-2-methylbenzenesulfonamide
(
3)
Using the general procedure described above from 4.06 mL
ꢀ
5
ꢀ1
(0.08 mol) 1,5-diamino pentane and 2-methylbenzenesulphonyl
chloride 3.85 mL (0.04 mol) a white solid was obtained. The prod-
uct was filtered and recrystallized from a ethanol/n-hexane (4/1)
mixture and was dried in vacuo and stored under ethanol vapor:
Yield 80%; mp 183–184 °C; IR (KBr) cm : 3294
d(NH) 2947 (CH ), 1323 ), 1169
for C18 : C, 54.52; H, 6.10; N, 7.06; S, 16.17, Found: C,
4.51; H, 6.00; N, 7.00; S, 15.99.
1
.0 ꢁ 10 mol L and the samples were excited at 249 nm wave-
length. The photoluminescence quantum efficiencies of the com-
pounds calculated using 9.10-diphenylantracene as the standard
[
27–29].
ꢀ1
t
(NH), 1439
,
t
3
t
asym.(SO
2
tsym.(SO ); Anal. Calcd.
2
2
.2. General procedure for the synthesis
24 2 4 2
H N O S
5
Nucleophilic substitution reaction of the aromatic diamines
with arylsulfonyl chlorides were carried out as follows: THF solu-
tion of aromatic diamines were added slowly to THF solutions of
the sulfonyl chlorides at ꢀ5 °C. The reaction mixture was stirred
for 24 h at room temperature and completion of the reaction was
monitored by TLC. After the completion of the reaction, the solvent
was evaporated in vacuo. The solid residue was purified by column
chromatography.
2
.3. Structure optimizations
All calculations were performed using a Pentium IV computer
with default convergence criteria and Gaussian 03 software pack-
age [30]. An extensive search for low energy conformations on po-
tential energy surfaces (PES) of compounds were carried out by
using a systematic search with RHF/6-31G(d,p) levels. Minimum
energy conformations were re-optimized at DFT/B3LYP/6-
311+G(d,p) levels without symmetry constraints. Vibration fre-
quencies calculated ascertain the structure to be stable (no imagi-
nary frequencies).
0
2
.2.1. Synthesis of N,N -butanediyl-bis-2-methylbenzenesulfonamide
(
1)
Using the general procedure described above from 4.06 mL
0.08 mol) 1,4-diamino butane and 2-methylbenzenesulphonyl
(

S. Alyar et al. / Journal of Molecular Structure 992 (2011) 27–32
29
2
.4. Micro dilution assays
data for half of the compounds are given in Tables 1 and 2, respec-
tively. It is known that symmetric C and H atoms in the compounds
show the same chemical shift due to them having same chemical
E. coli ATCC 11230, S. enterititis ATCC 13076, S. aureus ATCC
5923, B. cereus ATCC 6633 and B. magaterium RSKK 5117 cultures
1
2
environment. H NMR spectrum of (1) was obtained using
were obtained from the Department of Biology at Gazi University
and the Refik Saydam Hygiene Center Culture Collection. Bacterial
strains were cultured overnight at 37 °C in Nutrient Broth. These
stock cultures were stored in the dark at 4 °C during the survey.
All tests were performed in a Nutrient Broth supplemented with
DMSO to a final concentration of 10% (v/v) to enhance their solubil-
ity. Test strains were suspended in the Nutrient Broth by adjusting
to the 0.5 McFarland standard. The compounds to be tested were
DMSO-d
at about 7.77–7.33 ppm. The chemical shift of the NH group the
compound in d -DMSO is in the range of 7.59 ppm however in
CDCl it is at about 4.48 ppm. Difference of chemical shift may be
6
. In NMR spectra, aromatic proton peaks were observed
6
3
attributed to the formation of intermolecular interactions with
the polar solvent DMSO.
The 13C NMR spectrum of (1) was obtained using DMSO-d
.
6
Molecule (1) has three different aliphatic carbon atoms and six aro-
matic carbon atoms. Magnetic shielding constants of C7 and
C8 atoms were observed at 41.73 ppm and 26.24 ppm, respec-
tively. Magnetic shielding constants of C7 atom were found to be
lower than the chemical shift value of C8 atom. Aromatic carbon
peaks are shown to be at about 126.07–138.71 ppm.
ꢀ1
dissolved in DMSO to give the highest concentration (450 lg mL ),
and serial dilutions thereafter in sterile 10 mL test tubes containing
nutrient broth to give sample concentrations of the range 45–
ꢀ1
4
50 lg mL . The minimum inhibitory concentration (MIC) values
of compounds were determined using a modification of the micro-
well dilution assay method. 96 well plates were prepared by dis-
The 2D COSY NMR spectrum of (1) was obtained using DMSO-
. The COSY spectrum confirms the above H spectral assign-
1
pensing 95
l
L of nutrient broth and 5
l
L of the inoculums into
d
6
each well. 100
l
L from test compounds initially prepared at
ments. The multiplet at d 1.30 ppm is for the H9–10 protons. In
the COSY spectrum horizontal and vertical lines drawn from at d
1.30 ppm met the off – diagonal peak at 2.68 ppm which was as-
signed to the H7–8 protons. Similarly the lines from the peak at
2.68 ppm met the off-diagonal peak at 1.30 ppm. This establishes
the fact that the protons at H9–10 split the peak of H7-8 protons into
multiple and vice versa because they are neighboring protons.
From 2D HETCOR NMR spectrum (Fig. 3), it is clear that the peaks
ꢀ1
4
1
50
00
l
g mL concentration were added into the first wells. Then,
l
L from the serial dilutions was transferred into fourteen con-
secutive wells. The contents of the wells were mixed and the micro-
plates were incubated at 37 °C for 24 h. The compounds were tested
against each microorganisms twice. The MIC values were deter-
mined from visual examinations as the lowest concentration of
the extracts in the wells with no bacterial growth [31].
1
3
at d values 138.71 and 136.42 in the C NMR spectrum did not
show any contour in HETCOR confirming that they are non proton-
ated and are assigned to C1 and C2. The correlations between C7–
2.5. Disc diffusion method
H
7–8, C8–H9–10 in the zigzag structure and C3–H
3 4 5
, C4–H , C5–H ,
Bacterial susceptibility testing was performed by the disc diffu-
C6–H in the aromatic ring are also observed in HETCOR spectrum.
6
sion method according to the guidelines of Clinical and Laboratory
Standards Institute (CLSI) [32]. The sterilized (autoclaved at 120 °C
for 30 min), liquefied Mueller Hinton agar (40–50 °C) was inocu-
lated with the suspension of the microorganism (matched to 0.5
McFarland) and poured into a Petri dish to give a depth of 3–
The IR spectra of the compounds were found to be very similar
to each other. More characteristic vibrations of the compound (1)
is as follows: asymmetric and symmetric stretching vibrations of
ꢀ1
SO
2
groups were observed at about 1317 and 1169 cm , respec-
tively. Terminal methyl stretching vibrations were noted at
4
(
mm. The paper discs impregnated with the test compounds
ꢀ1
2
3
979 cm . The presence of single and strong NH band at about
281 cm confirms the presence of secondary amine group in
60 g) were placed on the solidified medium. Discs were placed
l
ꢀ1
on agar plates and the cultures were incubated at 37 °C for 24 h
for bacteria. Inhibition zones formed on the medium were evalu-
the compound.
ated in mm. Ciprofloxacin (5 lg/disk) was chosen as a standard
in antibacterial activity measurements (positive control). DMSO
3.2. Fluorescence measurements
poured disk was used as negative control.
The optical properties of the compounds (1–3) were explored
using UV–Vis and PL. Absorption and photoluminescence spectra
3
. Results and discussion
were studied for solutions of compounds (1–3), excited at
2
49 nm. The most striking feature was that these compounds gave
3
.1. Structure analysis
an intense emission upon irradiation by UV light. The photolumi-
nescence spectrum of (1) in THF is shown in Fig. 2. Maximum lumi-
nescent intensity was observed at 405 nm and the full width at half
maximum was 121 nm. Compound (1) exhibited a photolumines-
6
NMR spectra of compounds were recorded in DMSO-d and
1
13
3
CDCl using TMS as the internal standard. H NMR and C NMR
Table 1
1
H NMR data for compounds (1–3).
Assignment
(1)
(2)
(3)
DMSO
CDCl
3
DMSO
CDCl
3
DMSO
CDCl
3
2
3
-CH
-CH
3
3
2.60 (s, 3H)
–
2.68 (t, 2H)
1.30 (t, 2H)
–
7.77 (d, H)
7.49 (t, H)
7.33 (t, 2H)
7.33 (t, 2H)
–
2.65 (s, 3H)
–
2.92 (t, 2H)
1.51 (p, 2H)
–
7.96 (d, H)
7.48 (t, H)
7.33 (t, 2H)
7.33 (t, 2H)
–
–
–
2.57 (s, 3H)
–
2.64 (s, 3H)
–
2.35 (s, 3H)
2.50 (t, 2H)
1.32 (q, 2H)
–
7.45 (d, H)
7.45 (d, H)
–
7.49 (t, H)
7.52 (s, H)
7.50
2.45 (s, 3H)
2.96 (t, 2H)
1.54 (q, 2H)
–
7.42 (d, H)
7.42 (d, H)
–
7.65 (t, H)
7.68 (s, H)
4.58
H
H
H
H
H
H
H
H
7
–H
–H10
8
2.68 (t, 2H)
1.25 (p, 2H)
1.12 (p, 2H)
7.81 (d, H)
7.48 (t, H)
7.36 (t, 2H)
7.36 (t, 2H)
–
2.89 (t, 2H)
1.41 (p, 2H)
1.29 (p, 2H)
7.95 (d, H)
7.46 (t, H)
7.31 (t, H)
7.31 (t, H)
–
9
11–H12
6
4
3
5
2
NH
7.59
4.48
7.56
4.94

3
0
S. Alyar et al. / Journal of Molecular Structure 992 (2011) 27–32
Table 2
between the aromatic rings. The photoluminescence spectrum of
1
3C NMR data for compounds (1–3).
compound (2) in THF is also shown in Fig. 2. Maximum luminescent
intensity was observed at 379 nm and the full width at half maxi-
mum was 126 nm. Compound (2) exhibited a photoluminescence
quantum yield of 45 ± 2.2% and a long excited-state lifetime of
4.17 ± 0.20 ns. The reason for the high quantum yields is due to
Assignment
(1)
(2)
(3)
2
3
-CH
-CH
3
19.75
–
–
19.75
–
3
20.80
42.03
26.17
–
140.42
126.63
132.82
123.55
128.96
138.79
C7
C8
C9
C1
C2
C4
C5
C6
C3
41.73
26.24
–
138.71
136.42
132.40
132.22
128.30
126.07
42.06
28.53
22.99
138.82
136.41
132.38
132.20
128.31
126.77
the resulting p-electrons extensive delocalizations in the chemical
structure of the compound. It can be seen in Fig. 2 that the maxi-
mum photoluminescence peak shifted to lower wavelength from
405 to 379 nm with the position of substituent on the aromatic
rings. Also, the shoulder peak at 296 on the excitation spectrum be-
comes more intense and obvious. This emission wavelength differ-
ence may be used for tuning properties in photoluminescent
devices. As seen in Fig. 2 for compound (3) maximum luminescent
intensity was observed at 402 nm and the full width at half maxi-
mum was 114 nm. Compound (3) exhibited a photoluminescence
quantum yield of 34 ± 1.4% and a long excited-state lifetime of
9
8
7
6
5
4
3
2
1
00
00
00
00
00
00
00
00
00
0
3
.15 ± 0.12 ns. The maximum luminescent intensity reduced and
Ex-(2)
Em-(2)
shifted to lower wavelength for longer chain length between the
aromatic rings. The photoluminescence data for the compounds
are summarized in Table 3. The quantum yields and excited-state
lifetimes of each compound was measured four times, and the re-
sults were averaged. Table 3 gives the quantum yields and ex-
cited-state lifetimes with their corresponding average deviations
among the four results. The deviations give an indication of the reli-
ability of the measurements. The average deviations of quantum
yields and lifetimes for all the compounds were less than 5%. The
photoluminescent properties of these compounds may indicate
great potential for numerous optical and electronic applications.
Ex-(1)
Ex-(3)
Em-(1)
Em-(3)
2
00
260
320
380
440
500
560
3.3. UV–Vis spectra
Wavelength (nm)
The UV–Vis spectra were calculated using TD-DFT and Zerner’s
intermediate neglect of differential overlap/spectroscopic (ZINDO/
S) methods. TD-DFT calculations were performed in the gas phase.
In the calculation of excited energies for the disulfonamides using
the B3LYP function, and the 6-31G(d,p), 6-31G+(d,p), 6-311G(d,p)
and 6-311+G(d,p) basis sets. The calculated maximum absorption
wavelengths and oscillator strengths are given in Table 4. For com-
pounds (1) and (3), kmax values were 234 nm [6-31G(d,p)], 239 nm
Fig. 2. Photoluminescence spectra of compounds (1–3) in THF; samples were
excited at 249 nm.
cence quantum yield of 39 ± 1.8% and a long excited-state lifetime
of 3.65 ± 0.16 ns. The reason for the high quantum yields is that
the
p-electrons extensive delocalizations form in the chemical
structure. Fig. 2 also shows the comparison of excitation and emis-
sion spectra of compounds (1–3) in the solvent THF. The photolumi-
nescence intensities and quantum yields of the compounds varied
with the position of the substituent on the ring and the chain length
[
6-31+G(d,p)], 237 nm [6-311G(d,p)] and 240 nm [6-311+G(d,p)].
For compound (2), these values are 237, 242, 240 and 243 nm.
The results which obtained using the B3LYP function and 6-
Table 3
Photoluminescence data for compounds (1–3).
Compound
kmax Ex (nm)
In Ex
k
max Em (nm)
In Em
/
f
(%)
f
s (ns)
(1)
(2)
(3)
259 (226;242;295)
260 (225;241;296)
259 (225;241;393)
652
759
554
405 (356;383;434)
379 (356;401;432)
402 (354;378;431)
645
751
546
39 ± 1.8
45 ± 2.2
34 ± 1.4
3.65 ± 0.16
4.17 ± 0.20
3.15 ± 0.12
k
k
max Ex: maximum excitation wavelength; In Ex: maximum excitation intensity.
max Em: maximum emission wavelength; In Em: maximum emission intensity.
f f
/ : quantum yield; s : excited-state lifetime.
Table 4
Calculated absorption maxima and oscillator strengths for compounds (1–3).
a
Compound
DFT/B3LYP
Expbkmax (nm)
ZNDO/S
6-31G(d,p)
6-31+G(d,p)
6-311G(d,p)
6–311+G(d,p)
(1)
(2)
(3)
244
252
244
273.65 (0.0646)
271.88 (0.0273)
273.7 (0.1012)
234.49 (0.0142)
237.13 (0.0178)
234.39 (0.0140)
239.15 (0.0164)
242.66 (0.0209)
239.1 (0.0164)
237.62 (0.010)
240.75 (0.0205)
237.53 (0.0148)
240.36 (0.0159)
243.97 (0.0211)
240.3 (0.0158)
a
Oscillator strengths are given in parenthesis.
In DMSO.
b

S. Alyar et al. / Journal of Molecular Structure 992 (2011) 27–32
31
Table 5
Antimicrobial activity of compounds (1–3) with microdilution method.
Compound
MIC (l
g mLꢀ1)
E. coli ATCC 11230
S. enterititis ATCC 13076
B. megaterium RSKK 5117
B. cereus ATCC 6633
S. aureus ATCC 25953
(
(
(
1)
2)
3)
90
112
180
125
157
300
360
380
430
125
157
310
112
134
250
Table 6
Result of the antimicrobial test of compounds (1–3); disk potency 60
lg.
Compound
Diameter of inhibition zone (mm)
E. coli ATCC 11230
S. enterititis ATCC 13076
B. megaterium RSKK 5117
B. cereus ATCC 6633
S. aureus ATCC 25953
(
(
(
1)
2)
3)
22
20
14
38
14
13
11
31
–
–
–
15
16
14
11
27
18
15
10
29
Ciprofloxacin (5
lg/disk)
3
11+G(d,p) basis set showed excellent agreement between the
found to exhibit intense photoluminescence at 405, 402 and
379 nm, respectively and the photoluminescence intensities and
quantum yields of the compounds varied with the position of sub-
stituent on the ring and the chain length between the aromatic
rings. These compounds are interesting materials for applications
in electroluminescent devices. The TD-DFT calculations were per-
formed using the B3LYP functional with the four different basis
sets 6-31G(d,p), 6-31+G(d,p) 6-311 G(d,p) and 6-311+G(d,p) and
yielded accurate results for the aromatic disulfonamides. The re-
sults obtained using the B3LYP functional showed an excellent
agreement between the experimental and calculated values of
experimental and calculated values of kmax. The kmax value ob-
tained with semi-empirical ZINDO/S for the compounds were high-
er than those obtained using the TD-DFT method. The length of the
carbon chain does not change the kmax of compounds. The kmax of
the compounds varies with the position of substituent on the ring.
The meta position of kmax order of aromatic disulfonamides is
greater than ortho.
3.4. Antibacterial activity
Synthesized compounds (1–3) were screened for antibacterial
kmax. Compounds showed broad spectrum antimicrobial activity,
activity against Gram-positive bacteria (S. aureus ATCC 25923, B.
cereus ATCC 6633 and B. megaterium RSKK 5117) and Gram-nega-
tive bacteria (E. coli ATCC 11230 and S. enterititis ATCC 13076) by
disk diffusion and microdilution methods. The antibacterial activ-
ity results are given in Tables 5 and 6. Results indicated that the
synthesized compounds possessed a broad spectrum of activity
against the tested microorganisms and showed relatively better
activity against Gram-negative than Gram- positive bacteria.
Compound (1) showed the highest activity with lowest MIC val-
and activity decreased as the length of the carbon chain increased.
Compound (1) showed the best activity with the lowest MIC
ꢀ1
(420 lg mL ) against E. coli bacteria.
Acknowledgments
The authors wish to thank TUBITAK for the financial support
(TBAG 104 T 390 and (MAG 104M 367) and Gazi University Scien-
tific Research Project (05/2008-05). We would also like to thank
the Departments of Chemistry at Gazi University and Gaziantep
University.
ꢀ1
ꢀ1
ues, 90
lg mL , 125
lg mL
against Gram-negative bacteria
E. coli and S. enterititis, respectively. All compounds showed poor
activity against B. magaterium, and compound (3) exhibited the
ꢀ1
lowest inhibitory activity with a MIC of 430 lg mL . Among the
Appendix A. Supplementary material
compounds, compound (3) showed the lowest activity against all
test microorganisms. The results obtained revealed that the anti-
bacterial activity decreased as the length of the carbon chain in-
creased. However, aromatic disulfonamide compounds showed
decrease in antibacterial activity than sulfonyl hydrazide [19].
The primary amine group plays a more important role than sec-
ondary amine groups. Furthermore, antibacterial activity of aro-
matic disulfonamide compounds are higher than aliphatic
disulfonamides and sulfonyl hydrazones published in the literature
Supplementary data associated with this article can be found, in
the online version, at doi:10.1016/j.molstruc.2011.02.024.
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