Synthesis and laser activity of halo-acridinedione derivatives

Article abstract of DOI:10.1002/jhet.45

Synthesis of 10-(halophenyl)-9-(4-methoxyphenyl)-3, 4, 6, 7, 9, 10-hexahydroacridine-1, 8-(2H, 5H)-dione derivates have been prepared and their absorption, emission, and laser properties have been evaluated. The structures of all the synthesized compounds

Full text of DOI:10.1002/jhet.45

294
Synthesis and Laser Activity of Halo-Acridinedione Derivatives
Muharrem Kaya,a Yılmaz Yıldırır,a* and Lemi Tu¨rkerb
Vol 46
aDepartment of Chemistry, Faculty of Arts and Science, Gazi University, Ankara, Turkey
bDepartment of Chemistry, Faculty of Arts and Science, Middle East Technical University,
Ankara, Turkey
*E-mail: yildirir@gazi.edu.tr
Received September 28, 2007
DOI 10.1002/jhet.45
Published online 16 March 2009 in Wiley InterScience (www.interscience.wiley.com).
Synthesis of 10-(halophenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione
derivates have been prepared and their absorption, emission, and laser properties have been evaluated.
The structures of all the synthesized compounds were characterized by spectroscopic methods IR, 1H
NMR, 13C-APT, MS, and elemental analysis.
J. Heterocyclic Chem., 46, 294 (2009).
INTRODUCTION
together various halo-anilines with acetic acid-ammo-
nium acetate system in toluene for the syntheses of acri-
dinediones (Scheme 1). Acridinediones were obtained
with high yield (from 75 to 92%) and short reaction
time 2 h data for all compounds. Physical and analytical
data of compounds were given in Table 1.
Many organic compounds demonstrated laser activity
in the 310–1100 nm region [1]. These laser dyes have
been classified as xanthene dyes, cyanine or polyme-
thine dyes, linear and condensed polybenzoid com-
pounds, and heterocyclic compounds. In the heterocyclic
series, rhodamine, coumarin, and acridinedione have
been known as efficient laser dyes. So far, the acridine-
dione ring system reported possesses laser activity in the
475–500 nm region [2–5]. The effectiveness of lasing
can be controlled by substituents at the 9- and 10-posi-
tions of the acridine chromophore [6]. Therefore, acridi-
nediones with substituents at 9- or 10-positions have al-
ready been synthesized by using different methods [7–
13]. Photochemical properties of some acridinedione
dyes were reported in literature [14–16]. In this study,
we reported the synthesis of novel halogen substitute
acridinediones. In addition to UV, fluorescence spectra
and laser activity of the acridinedione dyes were exam-
ined (Table 1).
The purity of the compounds was checked by using
TLC. All of the products were characterized by IR,
1H NMR, 13C-APT, mass spectrometry, and elemental
analyses.
All spectral data are in accordance with assigned
structures. In IR spectra, aromatic CAH, aliphatic CAH,
and C¼¼O stretching bands were observed at expected
values. In the 1H NMR spectra, methyl protons were
seen at ꢀ0.85–1.10 ppm as two singlet peaks. Aromatic,
methylene, methane, and OCH3 protons were seen at
expected values. The 13C-APT spectra of the compounds
displayed the number of resonance that fit exactly with
the number of expected carbon resonances. Mass spectra
of the compounds were taken using the chemical ioniza-
tion (CI) technique. In general molecular ion peaks were
seen in spectra and the base peaks were found by cleav-
age of the aryl ring from the parent molecule. The struc-
ture of compounds IX was further confirmed by an X-
ray crystallographic analysis [17]. In summary, all com-
pounds show good florescence and laser activity in chlo-
roform (1 ꢁ 10ꢂ4M). Table 1 gives the absorption,
emission, and laser activity of the dyes that have high
RESULTS AND DISCUSSION
The tetraketones were formed by the condensation of
cyclohexane-1,3-dione or 5,5-dimethyl-1,3-cyclohexane-
dione
with
4-methoxybenzaldehyde
furnishing
compounds I and II. Then, tetraketones were refluxed
C
V
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Synthesis and Laser Activity of Halo-Acridinedione Derivates
295
Table 1
Yields, melting points, UV, fluorescence, laser, and elemental analyses data for III–XIV.
Elemental analyses
(%) Calc./Found
Yield
(%)
kUV
(nm)
kFlu
(nm)
klaser
(nm)
Molecular
formula
Compound
X
R
H
mp (ꢃC) (Ref.)
265–266
C
H
N
III
4-F
79
90
77
92
85
77
75
80
90
81
86
75
272, 356
238, 360
242, 361
243, 357
247, 361
240, 358
244, 364
248, 367
247, 366
250, 369
249, 369
240, 363
424
431
443
423
422
423
433
434
421
425
427
422
554
546
548
558
534
540
535
550
530
542
530
536
C26H24FNO3
C26H24ClNO3
C26H24ClNO3
C26H24BrNO3
C26H24INO3
C30H32FNO3
C30H32FNO3
C30H32ClNO3
C30H32ClNO3
C30H32BrNO3
C30H32BrNO3
C30H32INO3
74.80
74.51
71.97
71.70
71.97
71.89
65.28
65.20
59.44
59.37
76.08
75.85
76.08
76.01
73.53
73.36
73.53
73.45
67.41
67.20
67.41
67.28
61.97
61.78
5.79
5.77
5.57
5.55
5.57
5.49
5.06
5.04
4.60
4.58
6.81
6.79
6.81
6.77
6.58
6.56
6.58
6.56
6.03
6.01
6.03
5.97
5.55
5.53
3.36
3.34
3.23
3.19
3.23
3.22
2.93
2.89
2.67
2.66
2.96
2.93
2.96
2.95
2.86
2.81
2.86
2.82
2.62
2.60
2.62
2.61
2.41
2.39
IV
4-Cl
2-Cl
4-Br
4-I
H
283, 285 [18]
248
V
H
VI
H
217–219
242–243
230 (dec)
209
VII
VIII
IX
H
4-F
CH3
CH3
CH3
CH3
CH3
CH3
CH3
2-F
X
4-Cl
2-Cl
4-Br
2-Br
4-I
220–221
245
XI
XII
XIII
XIV
245, 247–248 [19]
268
263, 259–263 [20]
obtained with Varian CARY Eclipse Fluorescence Spectropho-
tometer. The dye solutions (in a 2 cm ꢁ 2 cm quartz cell)
were excited by using Ar ion laser; its wavelength was 488
nm and the pulse duration 6 ns and were detected by a diode.
All measurements were performed in the presence of air at
room temperature.
lasing efficiencies using chloroform as solvent. The tun-
ing range for the dyes lies between 530 and 558 nm
(Fig. 1).
General procedure. The syntheses of compounds I and II
were achieved according to the procedure described in the lit-
erature [20]. For that purpose, 4-methoxybenzaldehyde (3.40
g, 25 mmol) was added to the solution of cyclohexane-l,3-
dione (5.60 g, 50 mmol) in aq. methanol (20 mL) and warmed
until the solution became cloudy. The tetraketone started to
separate out. Then, the reaction mixture was diluted with water
to 250 mL and allowed to stand overnight; the tetraketone was
collected by filtration and dried and recrystallized from metha-
nol (I: yield 92%, mp 196ꢃC; lit. mp for I: 196ꢃC [20] and II:
yield 90%, mp 142–143ꢃC; lit. mp for II: 142–143ꢃC [21],
125.5–126.5ꢃC [21]).
EXPERIMENTAL
Melting points were measured on an Electrothermal 9100
apparatus. Absorption spectra were performed on an ATI Uni-
cam UV-100 spectrophotometer. Infrared absorption spectra
were recorded from a Mattson 1000-FTIR spectrometer, using
KBr pellets. 1H NMR (300 MHz) and 13C-APT (75 MHz)
spectra were obtained with a Bruker DPX-300 FT-NMR
instrument with CDCl3 as solvent. Mass spectra with CI were
recorded on a AGILENT 1100 MSD instrument. The elemen-
tal analyses (C, H, N) were conducted using the Elemental
Analyser LECO CHNS-932. Fluorescence spectra were
Scheme 1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

296
M. Kaya, Y. Yıldırır, and L. Tu¨rker
Vol 46
Figure 1. Fluorescence spectra of the dyes III–XIV.
55.12 (OCH3), 113.57 (CH), 113.28 (CH), 116.04 (C), 128.01
(CH), 129.59 (CH), 130.83 (CH), 130.97 (CH), 134.87 (C),
137.14 (C), 139.15 (C), 150.89 (C), 157.78 (C), 196.10 (C).
MS: m/z 433 (Mþ), 326 (Mþ-C6H4OCH3), 215 (Mþ-
C12H8ClOCH3).
10-(4-Fluorophenyl)-9-(4-methoxyphenyl)-3,4,6,7-hexa-
droacridine-1,8-(2H,5H-dione (III). The solution of 2,2’-((4-
methoxyphenyl)methylene) dicyclohexane-1,3-dione (I) (1.03
g, 3 mmol), 4-fluorobenzenamine (0.34 g, 3.0 mmol), and
excess amount of ammonium acetate were prepared with 20
mL toluene-acetic acid mixture (1:1). The formed solution was
refluxed for 2 h by using a Dean-Stark apparatus. Then, the
reaction mixture was poured into 100 mL water. Afterwards,
last mixture was taken to a separation flask and 25 mL CHCl3
was added. The organic phase was separated and evaporated.
Halo-acridinedione (III) was separated from residue by thin
layer chromatography and dried and then recrystallized from
CHCl3–MeOH (9:1). This compound was obtained as yellow
solid, mp 265–266ꢃC; IR: 3063 (Ar-H), 2954 (CAH), 1631
10-(4-Bromophenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-
hexadroacridine-1,8-(2H,5H)-dione (VI). This compound
was obtained as yellow solid (chloroform–methanol), mp 217–
219ꢃC. IR: 3031 (Ar-H), 2940 (CAH), 1638 (C¼¼O), 1573
1
(C¼¼C) cmꢂ1. H NMR: d 1.75–1.98 (m, 4H, 2 ꢁ CH2), 2.20–
2.47 (m, 8H, 4 ꢁ CH2), 3.90 (s, 3H, OCH3), 5.32 (s, 1H, CH),
6.80 (d, 2H, J ¼ 8.7 Hz, ArH), 7.17 (d, 2H, J ¼ 8.4 Hz,
ArH), 7.32 (d, 2H, J ¼ 8.7 Hz, ArH), 7.7 (d, 2H, J ¼ 8.4 Hz,
ArH). 13C-APT: d 21.10 (CH2), 28.33 (CH2), 31.18 (CH),
36.67 (CH2), 55.18 (OCH3), 113.52 (CH), 116.47 (C), 124.66
(C), 128.02 (CH), 131.20 (CH), 133.47 (CH), 137.59 (C),
138.75 (C), 151.00 (C), 157.86 (C), 196.10 (C). MS: m/z 477
(Mþ), 370 (Mþ-C6H4OCH3), 215 (Mþ-C12H8BrOCH3).
1
(C¼¼O), 1585 (C¼¼C) cmꢂ1. H NMR: d 1.73–1.97 (m, 4H, 2
ꢁ CH2), 2.03–2.47 (m, 8H, 4 ꢁ CH2), 3.77 (s, 3H, OCH3),
5.32 (s, 1H, CH), 6.82 (d, 2H, J ¼ 8.5 Hz, ArH), 7.18–7.36
(m, 6H, ArH). 13C-APT: d 21.10 (CH2), 28.33 (CH2), 31.18
(CH), 36.65 (CH2), 55.18 (OCH3), 113.63 (CH), 116.04 (C),
116.98 (CH), 129.33 (CH), 131.67 (CH), 135.07 (C), 138.79
(C), 151.30 (C), 160.90 (C), 164.23 (C), 196.14 (C). MS: m/z
417 (Mþ), 291 (Mþ-C6H4FOCH3).
10-(4-Iodophenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-hexa-
oacridine-1,8-(2H,5H)-dione (VII). This compound was
obtained as yellow solid (chloroform–methanol), mp 242–
243ꢃC. IR: 3050 (Ar-H), 2940 (CAH), 1645 (C¼¼O), 1580
1
(C¼¼C) cmꢂ1. H NMR: d 1.72–1.96 (m, 4H, 2 ꢁ CH2), 2.18–
10-(4-Chlorophenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-
hexahydroacridine-1,8-(2H,5H)-dione (IV). This compound
was obtained as yellow solid (chloroform–methanol), mp
283ꢃC Ref. [17] 285ꢃC. IR: 3034 (Ar-H), 2947 (CAH), 1640
2.47 (m, 8H, 4 ꢁ CH2), 3.78 (s, 3H, OCH3), 5.29 (s, 1H, CH),
6.80 (d, 2H, J ¼ 8.7 Hz, ArH), 7.04 (d, 2H, J ¼ 8.4 Hz,
ArH), 7.32 (d, 2H, J ¼ 8.7 Hz, ArH), 7.88 (d, 2H, J ¼ 8.4
Hz, ArH): 13C-APT: d 21.04 (CH2), 28.36 (CH2), 31.19 (CH),
36.41 (CH2), 55.19 (OCH3), 95.13 (C), 113.67 (CH), 116.12
(C), 128.67 (CH), 131.35 (CH), 138.49 (C), 138.71 (C),
139.24 (CH), 151.44 (C), 157.92 (C), 196.23 (C). MS: m/z 525
(Mþ), 418 (Mþ-C6H4OCH3).
1
(C¼¼O), 1573 (C¼¼C) cmꢂ1. H NMR: d 1.76–2.00 (m, 4H, 2
ꢁ CH2), 2.05–2.47 (m, 8H, 4 ꢁ CH2), 3.78 (s, 3H, OCH3),
5.34 (s, 1H, CH), 6.78 (d, 2H, J ¼ 8.7 Hz, ArH), 7.20 (d, 2H,
J ¼ 8.5 Hz, ArH), 7.33 (d, 2H, J ¼ 8.7 Hz, ArH), 7.54 (d,
2H, J ¼ 8.5 Hz, ArH). 13C-APT: d 21.10 (CH2), 28.33 (CH2),
31.18 (CH), 36.67 (CH2), 55.18 (OCH3), 113.50 (CH), 116.07
(C), 128.66 (CH), 129.32 (CH), 130.80 (CH), 135.49 (C),
137.59 (C), 138.75 (C), 151.00 (C), 157.86 (C), 196.10 (C).
MS: m/z 433 (Mþ), 326 (Mþ-C6H4OCH3).
10-(4-Fluorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetra-
methyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione
(VIII). This compound was obtained as yellow solid (chloro-
form–methanol), dec. 230ꢃC. IR: 3028 (Ar-H), 2944 (CAH),
1637 (C¼¼O), 1580 (C¼¼C) cmꢂ1
.
1H NMR: d 0.86 (s, 6H, 2
ꢁ CH3), 1.02 (s, 6H, 2 ꢁ CH3), 1.80–2.06 (d, 4H, 2 ꢁ CH2),
2.25–2.40 (d, 4H, 2 ꢁ CH2), 3.83 (s, 3H, OCH3), 4.71 (s, 1H,
CH), 6.76 (d, 2H, J ¼ 8.5 Hz, ArH), 7.20–7.37 (m, 6H, ArH).
13C-APT: d 26.92 (CH3), 27.33 (CH3), 29.30 (CH), 32.21 (C),
41.85 (CH2), 50.10 (CH2), 55.14 (OCH3), 113.50 (CH), 115.07
(C), 123.47 (C), 128.77 (CH), 131.27 (CH), 133.40 (CH),
138.15 (C), 138.44 (C), 149.05 (C), 157.71 (C), 195.87 (C).
MS: m/z 473 (Mþ), 378 (Mþ-C6H4F), 271 (Mþ-C12H8FOCH3).
10-(2-Chlorophenyl)-9-(4-methoxyphenyl)-3,4,6,7,9,10-
hexahydroacridine-1,8-(2H,5H)-dione (V). This compound
was obtained as yellow solid (chloroform–methanol), mp
248ꢃC. IR: 3030 (Ar-H), 2940 (CAH), 1635 (C¼¼O), 1575
1
(C¼¼C) cmꢂ1. H NMR: d 1.66–1.94 (m, 4H, 2 ꢁ CH2), 2.25–
2.59 (m, 8H, 4 ꢁ CH2), 3.68 (s, 3H, OCH3), 4.56 (s, 1H, CH),
6.81 (d, 2H, J ¼ 8.5 Hz, ArH), 7.28–7.38 (m, 6H, ArH). 13C-
APT: d 21.18 (CH2), 26.54 (CH2), 31.45 (CH), 36.79 (CH2),
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Synthesis and Laser Activity of Halo-Acridinedione Derivates
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27.30 (CH3), 29.75 (CH), 31.82 (C), 41.84 (CH2), 50.76
(CH2), 55.15 (OCH3), 113.60 (CH), 115.02 (C), 126.43 (C),
129.14 (CH), 130.70 (CH), 132.18 (CH), 132.45 (CH), 134.51
(CH), 138.21 (C), 138.47 (C), 147.82 (C), 157.49 (C), 195.82
(C). MS: m/z 533 (Mþ), 426 (Mþ-C6H4OCH3), 347 (Mþ-
C6H4OCH3Br).
10-(2-Fluorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetra-
methyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione
(IX). This compound was obtained as yellow solid (ethanol),
mp. 209ꢃC. IR: 3032 (Ar-H), 2944 (CAH), 1645 (C¼¼O), 1575
1
(C¼¼C) cmꢂ1. H NMR: d 0.85 (s, 6H, 2 ꢁ CH3), 0.91 (s, 6H,
2 ꢁ CH3), 1.64 (s, 2H, CH2), 2.09–2.24 (m, 6H, 3 ꢁ CH2),
3.75 (s, 3H, OCH3), 5.21 (s, 1H, CH), 6.79 (d, 2H, J ¼ 8.4
Hz, ArH), 7.27 (d, 1H, ArH), 7.49–7.52 (m, 4H, ArH), 7.68
(d, 1H, ArH). 13C-APT: d 26.80 (CH3), 29.30 (CH3), 30.96
(CH), 32.48 (C), 40.63 (CH2), 50.76 (CH2), 55.14 (OCH3),
113.46 (CH), 115.07 (C), 116.75 (CH), 117.02 (CH), 128.78
(CH), 129.31 (CH), 131.37 (CH), 138.46 (C), 140.48 (C),
140.60 (C), 40.87 (C), 157.73 (C), 195.88 (C). MS: m/z 472
(Mþ-H), 366 (Mþ-C6H4OCH3), 347 (Mþ-C6H4OCH3F).
Acknowledgment. The authors gratefully acknowledge the sup-
port provided by Turkey Republic State Planning Organization
under 2003K120470-39.
REFERENCES AND NOTES
10-(4-Chlorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetra-
methyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione
(X). This compound was obtained as yellow solid (chloro-
form–methanol), mp 220–221ꢃC. IR: 3030 (Ar-H), 2940
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1
(CAH), 1638 (C¼¼O), 1580 (C¼¼C) cmꢂ1. H NMR: d 0.9 (s,
6H, 2 ꢁ CH3), 1.1 (s, 6H, 2 ꢁ CH3), 2.09–2.36 (m, 8H, 4 ꢁ
CH2), 3.73 (s, 3H, OCH3), 4.71 (s, 1H, CH), 6.77 (d, 2H, J ¼
8.5 Hz, ArH), 7.16 (d, 2H, J ¼ 8.5 Hz, ArH), 7.25 (d, 2H, J
¼ 8.6 Hz, ArH), 7.46 (d, 2H, J ¼ 8.6 Hz, ArH). 13C-APT: d
27.33 (CH3), 29.27 (CH3), 30.97 (CH), 32.20 (C), 40.86
(CH2), 50.77 (CH2), 55.11 (OCH3), 113.48 (CH), 115.79 (C),
121.03 (C), 123.04 (CH), 129.00 (CH), 129.30 (CH), 136.45
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C12H8ClOCH3CH3).
(Mþ),
271
(Mþ-C12H8ClOCH3),
256
(Mþ-
10-(2-Chlorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetra-
methyl-3,4,6,7,9,10-hexahydroacridine-1,8-(2H,5H)-dione
(XI). This compound was obtained as yellow solid (ethanol),
mp. 245ꢃC. IR: 3042 (Ar-H), 2955 (CAH), 1640 (C¼¼O), 1585
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1
(C¼¼C) cmꢂ1. H NMR: d 0.84 (s, 6H, 2 ꢁ CH3), 0.92 (s, 6H,
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2 ꢁ CH3), 1.63 (s, 2H, CH2), 2.05–2.20 (d, 6H, 3 ꢁ CH2),
3.74 (s, 3H, OCH3), 5.17 (s, 1H, CH), 6.77 (d, 2H, J ¼ 8.7
Hz, ArH), 7.32 (d, 1H, ArH), 7.45–7.52 (m, 4H, ArH), 7.63
(d, 1H, ArH). 13C-APT: d 26.28 (CH3), 30.11 (CH3), 32.46
(C), 32.84 (CH), 41.77 (CH2), 50.01 (CH2), 55.09 (OCH3),
113.21 (CH), 115.04 (C), 128.79 (CH), 129.67 (CH), 130.80
(CH), 130.91 (CH), 131.17 (CH), 134.70 (C), 136.57 (C),
138.72 (C), 148.31 (C), 157.65 (C), 195.81 (C). MS: m/z 489
(Mþ), 474 (Mþ-CH3), 367 (Mþ-CH3C6H4OCH3).
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(XIII). This compound was obtained as yellow solid (ethanol),
mp. 268ꢃC. IR: 3049 (Ar-H), 2955 (CAH), 1660 (C¼¼O), 1595
[19] Wang, X. S.; Zhang, M. M.; Jiang, H.; Shi, D. Q.; Tu,
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[21] Horning, E. C.; Horning, M. G. J Org Chem 1946, 11, 95.
1
(C¼¼C) cmꢂ1. H NMR: d 0.87 (s, 6H, 2 ꢁ CH3), 0.94 (s, 6H,
2 ꢁ CH3), 1.77 (s, 2H, CH2), 1.92–2.07 (d, 2H, CH2), 2.35–
2.47 (d, 4H, 2 ꢁ CH2), 3.70 (s, 3H, OCH3), 5.20 (s, 1H, CH),
6.77 (d, 2H, J ¼ 8.5 Hz, ArH), 7.31 (d, 1H, ArH), 7.42–7.60
(m, 4H, ArH), 7.85 (d, 1H, ArH). 13C-APT: d 26.79 (CH3),
¨ ¨
[22] Bu¨yu¨kgongor, O.; Kaya, M.; Odabasoglu, M.; Yildirir, Y.
Acta Cryst (E) 2007, E63, 2275.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet