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1

Supplementary Information for

One-Pot, Efficient and Green Synthesis of Acridinedione Derivatives using Highly Monodisperse Platinum Nanoparticles

Supported with Reduced Graphene Oxide

Burak Aday a,†, Yunus Yıldız b,†, Ramazan Ulus a, Sinan Eris b, Fatih Sen b*, Muharrem Kayab*

a Chemistry Department, Faculty of Arts and Science, Dumlupınar University, Evliya Çelebi Campus 43100 Kütahya,

Turkey

b Sen Research Group, Biochemistry Department, Faculty of Arts and Science, Dumlupınar University, Evliya Çelebi

Campus 43100 Kütahya, Turkey..

Corresponding author: [email protected]

Materials and Instrumentation

PtCl4 (99 % Alfa Aesar), tetrahydrofuran (THF) (99.5 %, Merck) and ethanol (99.9 %) were purchased from Merck, 1-

octanamine (Sigma Aldrich) were used as received from suppliers. THF was distilled over sodium under argon atmosphere

and stored under inert atmosphere. De-ionized water was filtered by Millipore water purification system (18 MΩ) analytical

grade. All glassware and Teflon-coated magnetic stir bars were cleaned with aqua regia, followed by washing with distilled

water before drying in an oven.

The chemicals used in the synthesis of acridinedione derivatives were obtained from Merck and Aldrich Chemical Company.

All chemicals and solvents used for the synthesis were of spectroscopic reagent grade.

Transmission electron microscopy (TEM) images were obtained on a JEOL 200 kV TEM instrument. Sample preparation for

TEM analysis involves placement of a drop of 0.5 mg/mL ethanol solution of the prepared catalysts with a carbon support

on a carbon covered 400-mesh copper grid; the solvent is then allowed to evaporate. Excess solution was removed with an

adsorbent paper and the sample was dried under vacuum at room temperature before analysis. More than 300 particles

were calculated to get the integrated information about the overall distribution of Pt-based catalyst sample.

Thermo Scientific spectrometer was used for X-ray Photoelectron Spectroscopy (XPS) measurements and the X-ray

source was Kα lines of Mg (1253.6 eV, 10 mA). Samples were prepared by depositing the catalyst on Cu double-sided

tape (3M Inc.). C 1s line at 284.6 eV was chosen as a reference point and all XPS peaks were fitted using a Gaussian

function and the C 1s line at 284.6 eV was used as the reference line.

A Panalytical Emperian diffractometer with Ultima+theta–theta high resolution goniometer, having an X-ray generator

(Cu Kα radiation, k = 1.54056 Å) and operating condition of 45 kV and 40 mA, were employed in XRD analysis.

Raman spectrum was carried out using an in via Raman microprobe (Renishaw Instruments) with 514 nm laser excitation.

Melting points were measured on a Bibby Scientific Stuart Digital, Advanced, and SMP30. Fourier Transform Infrared (FT–IR)

spectra were recorded on Bruker Optics, ALPHA FT–IR spectrometer. The 1H-NMR and 13C-NMR spectra were obtained in

DMSO-d6 with Bruker DPX-300 as solvents with tetramethylsilane as the internal reference. The mass analyses were

Electronic Supplementary Material (ESI) for New Journal of Chemistry.This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

2

performed on an Agilent Technologies 6530 Accurate-Mass Q-TOF LC/HRMS at the advanced technology research centre of

Dumlupınar University (ILTEM).

Characterization of Pt NPs@rGO

Fig. S1 Low-magnification TEM images of the Pt NPs@rGO

Fig. S2. XRD of Pt NPs@rGO

3

Fig. S3. Pt 4f electron spectra of Pt NPs@rGO

Fig. S4. XPS spectra of C 1s for Pt NPs@rGO and GO

4

Fig. S5. The Raman spectra of Pt NPs@rGO (a) and RGO (b)

Table S1. The effect of molar ratio (Pt/rGO) on model reaction in the presence of Pt NPs@rGO

Entry R R’ Time(min) Yield (%)Pt/rGO

4a -H 4-Cl 60 94 1

4a -H 4-Cl 60 90 0.7

4a -H 4-Cl 60 84 0.5

Characterization of acridinedione derivatives

Whereas the infrared (IR) spectra of the novel synthesized 1, 8-dioxoacridine compounds (4i and 4j) aromatic C–H

stretching bands are observed between 3056 and 3018 cm−1, the aliphatic C–H stretching bands were observed between

2959 and 2955 cm−1. The compound 4i of cyan bond was showed at 2223 cm-1 and the carbonyl group bonds of compounds

4i and 4j were showed sharp peaks between 1632 and 1634 cm−1, respectively.

The 1H-NMR spectra of the compounds 4i and 4j belonging to protons of the methyl groups showed singlet peaks between

0.70-0.90 ppm. The methane (-CH2) protons of compounds 4i and 4j were observed in the region between 1.77-2.21 ppm.

The signals for the -CH protons of all compounds were observed between 4.95–5.10 ppm and the signals for the aromatic

protons were observed in the range between 6.61-7.70 ppm. The hydroxyl (-OH) proton of the compound 4j was showed at

9.05 ppm.

The signals observed in 13C-NMR (APT) spectrums of all novel acridinedione molecules (4i and 4j) are determined to be in

line with the recommended molecule structures. Further, when their high resolution mass spectra (HRMS) are examined,

the observed molecule ion peaks are in compliance with the recommended structures.

5

10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (4a)

N

O O

Cl

As yellow crystals, mp. (300-302 oC) [30] (ethanol). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 0.72 (s, 6H, 2x-CH3), 0.88 (s, 6H,

2x-CH3), 1.78 (d, 2H, J= 17.43 Hz, -CH2), 2.00 (d, 2H, J= 16.00 Hz, -CH2), 2.16-2.22 (m, 4H, -CH2), 5.05 (s, 1H, -CH), 7.07-7.12

(m, 1H, Ar-H), 7.21-7.32 (m, 4H, Ar-H), 7.48 (d, 2H, J= 5.44 Hz, 10.58, Ar-H), 7.68 (d, 2H, J= 8.84 Hz, Ar-H); 13C-NMR (75 MHz,

DMSO–d6) δ (ppm): 26.50, 29.72, 32.33, 32.44, 41.35, 50.03, 113.55, 126.26, 127.97, 128.38, 130.56, 134.37, 137.79,

146.57, 150.58, 195.54; IR (cm–1): 3026 w (Ar-H), 2954 s (-CH), 1634 s (C=O), 1590 s (C=C); HRMS (QTOF-ESI): m/z

C29H30ClNO2: 459.1965; found: 460.2061 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\.12 DBENZ4CL Instrument type and / or accessory 4/16/2014

3055

.37

3026

.78

2954

.76

2933

.83

2887

.39

2866

.99

1634

.89

1590

.96

1574

.99

1491

.57

1454

.00

1423

.80

1408

.81

1361

.30

1337

.31

1299

.20

1276

.06

1258

.88

1218

.16

1174

.80

1143

.70

1122

.36

1107

.75

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6x10

0.75

1

1.25

1.5

1.75

2

2.25

2.5

2.75

3

3.25

+ESI Scan (0.274 min) Frag=165.0V DBENZ4Cl_poz.d

* 460.2061

Counts vs. Mass-to-Charge (m/z)100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680 700 720 740 760 780 800 820 840 860 880 900 920 940 960 980 1000

Fig. S6. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4a

8

10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(4-nitrophenyl)-3,4,6,7,9,10 hexahydroacridine-1,8(2H,5H)-dione (4b)

N

O O

Cl

NO2



(m, 4H, Ar-H), 7.70 (d, 2H, J= 8.51 Hz, Ar-H), 8.14 (d, 2H, J= 8.68 Hz, Ar-H); 13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.57,

29.61, 32.47, 33.35, 41.39, 49.86, 112.51, 119.43, 123.76, 129.43, 134.55, 137.55, 146.16, 151.32, 154.01, 195.53; IR (cm–1):

3054 w (Ar-H), 2958 w (-CH), 1632 s (C=O), 1592 w (C=C); HRMS (QTOF-ESI): m/z calcd. For C29H29ClN2O4: 504.1816; found:

527.1729 ([M+Na]+).

a)

C:\OPUS_7.0.129\MEAS\20141113\.0 DA-4NO2 Instrument type and / or accessory 11/13/2014

3054

.22

2958

.40

2931

.37

2869

.16

2322

.26

1632

.86

1592

.72

1576

.22

1514

.22

1489

.34

1470

.06

1425

.73

1359

.41

1339

.77

1302

.47

1277

.57

1263

.58

1219

.62

1176

.44

1143

.89

1119

.70

1105

.71

1087

.48

1012

.80

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6x10

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0.8

1

1.2

1.4

1.6

1.8

2

2.2

2.4

2.6

2.8

3

3.2

3.4

3.6

3.8

4

+ESI Scan (1.682 min) Frag=165.0V I4CL4NO2_POZ.d

527.1729

505.1908

550.2491437.1955 595.1604 910.3339731.1356663.1477382.1585 481.3712 985.7558226.9526 799.1227121.0518 182.1656 274.2753

Counts vs. Mass-to-Charge (m/z)100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800 825 850 875 900 925 950 975 1000

Fig. S7. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4b

11

10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,6,7,9,10 hexahydroacridine-1,8(2H,5H)-dione (4c)

N

O O

Cl

NO2


2x-CH3), 1.82 (d, 2H, J= 17.44 Hz, -CH2), 2.02 (d, 2H, J= 16.04 Hz, -CH2), 2.20 (d, 2H, J= 3.30 Hz, -CH2), 2.25 (d, 2H, J= 4.95 Hz, -

CH2), 5.15 (s, 1H, -CH), 7.51-7.61 (m, 3H, Ar-H), 7.72 (d, 2H, J= 8.79 Hz, Ar-H), 7.78 (d, 1H, J= 7.87 Hz, Ar-H), 7.99-8.03 (m, 1H,

Ar-H), 8.12-8.13 (m, 1H, Ar-H) ); 13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.47, 29.62, 32.52, 32.92, 41.34, 49.84, 112.72,

121.50, 122.56, 130.21, 130.65, 134.58, 134.75, 137.52, 147.88, 148.60, 151.39, 195.63; IR (cm–1): 3049 w (Ar-H), 2956 w (-

CH), 1636 s (C=O), 1576 s (C=C); HRMS (QTOF-ESI): m/z calcd. For C29H29ClN2O4: 504.1816; found: 527.1655 ([M+Na]+).

a)

C:\OPUS_7.0.129\MEAS\20141113\.3 DA-3NO2 Instrument type and / or accessory 11/13/2014

3049

.53

2956

.72

2868

.91

2321

.01

2078

.02

1904

.34

1636

.16

1576

.08

1522

.95

1489

.34

1470

.65

1423

.22

1347

.94

1303

.04

1277

.92

1260

.97

1217

.99

1175

.96

1141

.83

1120

.32

1090

.43

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1.2

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1.6

1.8

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2.4

2.6

2.8

3

3.2

3.4

3.6

3.8

4

4.2

4.4

4.6

4.8

5

5.2

5.4

5.6

5.8

6

+ESI Scan (1.716 min) Frag=165.0V DA3NO2_POZ.d

527.1655

505.1841595.1524 731.1240433.2312325.2255 663.1382 937.4034780.2535122.0963 867.0956226.9501 997.6850821.5840182.1627

Counts vs. Mass-to-Charge (m/z)100 125 150 175 200 225 250 275 300 325 350 375 400 425 450 475 500 525 550 575 600 625 650 675 700 725 750 775 800 825 850 875 900 925 950 975 1000

Fig. S8. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4c

14

9-(4-Bromophenyl)-10-(4-chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10 hexahydroacridine-1,8(2H,5H)-dione (4d)

N

O O

Cl

Br


2x-CH3), 1.78 (d, 2H, J= 17.47 Hz, -CH2), 2.01 (d, 2H, J= 16.05 Hz, -CH2), 2.16-2.19 (m, 4H, -CH2), 5.00 (s, 1H, -CH), 7.26 (d, 2H,

J= 8.42 Hz, Ar-H), 7.42-7.50 (m, 4H, Ar-H), 7.68 (d, 2H, J= 8.77 Hz, Ar-H); 13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.56, 29.66,

32.27, 32.45, 41.35, 49.96, 113.08, 119.25, 130.33, 130.54, 131.26, 134.44, 137.67, 145.96, 150.81, 195.54; IR (cm–1): 3062

w (Ar-H), 2956 w (-CH), 1635 s (C=O), 1576 s (C=C); HRMS (QTOF-ESI): m/z calcd. For C29H29BrClNO2: 537.1070; found:

538.1123 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\20141112\.14 DA4Br Instrument type and / or accessory 11/12/2014

3062

.32

2956

.17

2932

.39

2869

.42

2322

.89

2206

.40

2103

.24

1985

.03

1897

.88

1635

.04

1576

.68

1504

.96

1485

.47

1470

.05

1414

.27

1358

.63

1302

.38

1279

.18

1262

.46

1216

.36

1176

.21

1145

.27

1117

.87

1094

.02

1009

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d)

Fig. S9. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4d

2x10

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1

1.1

1.2

1.3

1.4

+ESI Scan (1.755 min) Frag=165.0V N2_POZ.d

540.1113

665.1147562.0935418.1778 945.2203293.1748 990.1898346.0628 620.0566382.1562 453.0856 883.1713789.2330250.0994 493.1438 735.9672136.1130 836.2123188.1652

Counts (%) vs. Mass-to-Charge (m/z)100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680 700 720 740 760 780 800 820 840 860 880 900 920 940 960 980 1000

17

10-(4-Chlorophenyl)-9-(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8 (2H,5H)-dione (4e)

N

O O

Cl

F


2x-CH3), 1.78 (d, 2H, J= 17.43 Hz, -CH2), 2.01 (d, 2H, J= 16.08 Hz, -CH2), 2.16-2.22 (m, 4H, -CH2), 5.05 (s, 1H, -CH), 7.05 (t, 2H,

J= 8.84 Hz, Ar-H), 7.29-7.34 (m, 2H, Ar-H), 7.48 (d, 2H, J= 7.15 Hz, Ar-H), 7.68 (d, 2H, J= 8.70 Hz, Ar-H); 13C-NMR (75 MHz,

DMSO–d6) δ (ppm): 26.52, 29.68, 31.84, 32.45, 41.35, 49.98, 113.42, 114.86, 129.79, 130.53, 134.42, 137.72, 142.80,

150.64, 159.29, 195.55; IR (cm–1): 3054 w (Ar–H), 2957 s (-CH), 1637 s (C=O), 1576 s (C=C); HRMS (QTOF-ESI): m/z calcd. For

C29H29ClFNO2: 477.1871; found: 478.1956 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\.5 DA4F Instrument type and / or accessory 4/16/2014

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.69

2957

.08

2869

.58

1637

.70

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.53

1591

.43

1576

.83

1504

.31

1490

.53

1471

.28

1425

.56

1359

.08

1299

.97

1278

.15

1259

.88

1216

.78

1176

.58

1151

.26

1142

.06

1121

.45

1104

.81

1089

.25

1016

.24

999.

1398

3.24

937.

0692

0.62

886.

0486

3.80

853.

3184

0.07

815.

9080

0.12

781.

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6x10

0.2

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0.5

0.6

0.7

0.8

0.9

1

1.1

1.2

+ESI Scan (0.377 min) Frag=165.0V DA4F_poz.d

478.1956


Fig. S10. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4e

20

10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (4f)

N

O O

Cl

CH3


2x-CH3), 1.76 (d, 2H, J= 17.29 Hz, -CH2), 1.97-2.22 (m, 9H, -CH2 and –CH3), 5.00 (s, 1H, -CH), 7.04 (d, 2H, J= 8.05 Hz, Ar-H),

7.18 (d, 2H, J= 8.00 Hz, Ar-H), 7.35-7.55 (m, 2H, Ar-H), 7.68 (d, 2H, J= 8.82 Hz, Ar-H); 13C NMR (75 MHz, DMSO–d6) δ (ppm):

26.53, 29.15, 31.83, 32.32, 32.43, 41.33, 50.05, 113.69, 127.87, 128.40, 128.96, 134.34, 135.10, 137.83, 143.69, 150.43,

195.54; IR (cm–1): 3050 w (Ar-H), 2952 w (-CH), 1636 s (C=O), 1577 s (C=C); HRMS (QTOF-ESI): m/z calcd. For C30H32ClNO2:

473.2122; found: 474.2215 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\.10 DA4CH3 Instrument type and / or accessory 4/16/2014

3050

.29

2952

.38

2933

.10

2867

.97

2323

.55

1636

.30

1577

.23

1509

.54

1490

.99

1472

.80

1447

.81

1423

.16

1405

.75

1387

.87

1358

.55

1302

.22

1278

.31

1262

.68

1218

.44

1177

.67

1144

.53

1123

.06

1104

.18

1088

.97

1014

.88

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d)

6x10

0.6

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1

1.2

1.4

1.6

1.8

2

2.2

2.4

2.6

2.8

+ESI Scan (0.274 min) Frag=165.0V DA-4CH3_poz.d

* 474.2215


Fig. S11. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4f

24

10-(4-Chlorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro acridine-1,8(2H,5H)-dione (4g)

N

O O

Cl

OCH3


2x-CH3), 1.76 (d, 2H, J= 17.40 Hz, -CH2), 1.97-2.22 (m, 6H,-CH2), 3.70 (s, 1H, -OCH3), 4.95 (s, 1H, -CH), 6.80 (d, 2H, J= 8.62 Hz,

Ar-H), 7.20 (d, 2H, J= 8.61 Hz, Ar-H), 7.40-7.55 (m, 2H, Ar-H), 7.68 (d, 2H, J= 8.78 Hz, Ar-H); 13C NMR (75 MHz, DMSO–d6) δ

(ppm): 26.56, 29.73, 31.39, 32.44, 50.07, 55.31, 113.71, 113.83, 128.93, 130.56, 134.34, 137.85, 138.92, 150.28, 157.76,

195.55; IR (cm–1): 3006 w (Ar-H), 2951 w (-CH), 1638 s (C=O), 1577 s (C=C); HRMS (QTOF-ESI): m/z calcd. For C30H32ClNO3:

489.2071; found: 490.2160 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\.14 da-40ch3 Instrument type and / or accessory 4/16/2014

3052

.20

3006

.31

2951

.93

2905

.97

2869

.55

2837

.25

1638

.01

1609

.11

1577

.09

1507

.49

1490

.73

1471

.88

1439

.44

1422

.35

1392

.19

1358

.14

1298

.85

1277

.54

1258

.44

1232

.28

1217

.13

1171

.52

1139

.35

1118

.82

1105

.10

1088

.10

1036

.66

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1

1.21.4

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1.8

22.2

2.4

2.6

2.83

3.2

3.4

3.6

+ESI Scan (0.241 min) Frag=165.0V DA4OCH3_poz.d

* 382.1611

* 490.2160


Fig. S12. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4g

28

10-(4-Bromophenyl)-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (4h)

N

O O

Br



(m, 7H, Ar-H), 7.81 (d, 2H, J= 8.74 Hz, Ar-H); 13C-NMR (75 MHz, DMSO–d6) δ (ppm): 26.50, 29.71, 32.32, 32.45, 41.35, 50.03,

113.54, 123.01, 126.27, 127.97, 128.37, 133.54, 138.22, 146.57, 150.51, 195.54; IR (cm–1): 3028 s (Ar-H), 2954 s (-CH), 1634

s (C=O), 1575 s (C=C); HRMS (QTOF-ESI): m/z calcd. For C29H30BrNO2: 503.1460; found: 504.1529 ([M+H]+).

a)

C:\OPUS_7.0.129\MEAS\.6 DBENZ4BR Instrument type and / or accessory 4/16/2014

3085

.91

3054

.31

3028

.49

2954

.31

2933

.68

2886

.56

2866

.85

1634

.81

1575

.59

1488

.00

1469

.50

1454

.35

1423

.98

1403

.22

1361

.72

1299

.83

1276

.35

1259

.21

1218

.53

1175

.32

1142

.99

1122

.14

1107

.76

1067

.20

1012

.60

1000

.67

500100015002000250030003500Wavenumber cm-1

5060

7080

9010

0Tr

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ce [%

]

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c)

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d)

6x10

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1

1.1

+ESI Scan (0.341 min) Frag=165.0V DBENZ4BR_poz.d

504.1529

Counts vs. Mass-to-Charge (m/z)100 120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680 700 720 740 760 780 800 820 840 860 880 900 920

Fig. S13. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4h

31

4-(10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydro acridin-9-yl)benzonitrile (4i)

N

O O

Cl

CN

a)

C:\OPUS_7.0.129\MEAS\.7 DA4CN Instrument type and / or accessory 4/16/2014

3584

.05

3056

.91

2959

.06

2868

.09

2223

.46

2167

.46

2103

.86

1993

.10

1908

.13

1632

.27

1605

.58

1590

.84

1576

.20

1489

.37

1471

.70

1449

.09

1428

.96

1405

.40

1358

.12

1302

.33

1278

.25

1263

.38

1218

.97

1176

.94

1144

.53

1120

.27

1105

.08

1088

.57

1014

.70

1004

.01

500100015002000250030003500Wavenumber cm-1

6065

7075

8085

9095

100

Tran

smitt

ance

[%]

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b)

32

c)

33

d)

6x10

0.4

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0.8

1

1.2

1.4

1.6

1.8

+ESI Scan (0.260 min) Frag=165.0V DA4CN_poz.d

* 485.2006


Fig. S14. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4i

34

10-(4-Chlorophenyl)-9-(4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro acridine-1,8(2H,5H)-dione (4j)

N

O O

Cl

OH

a)

C:\OPUS_7.0.129\MEAS\.8 DA4OH Instrument type and / or accessory 4/16/2014

3342

.17

3093

.16

3062

.90

3018

.73

2955

.96

2936

.53

2882

.51

1634

.79

1621

.82

1610

.08

1589

.47

1566

.99

1509

.65

1492

.90

1481

.23

1441

.58

1423

.87

1406

.47

1385

.74

1362

.21

1313

.92

1299

.51

1273

.79

1259

.23

1245

.55

1218

.83

1165

.18

1143

.04

1121

.91

1100

.77

1084

.49

1014

.39

1000

.92

500100015002000250030003500Wavenumber cm-1

5560

6570

7580

8590

9510

0Tr

ansm

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ce [%

]

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b)

35

c)

36

d)6x10

0.4

0.6

0.8

1

1.2

1.4

1.6

1.8

2

2.2

2.4

+ESI Scan (0.226 min) Frag=165.0V DA4OH_poz.d

* 476.1997

382.1572


Fig. S15. a) FT-IR, b) 1H NMR, c) 13C NMR (APT), d) Q-TOF LC/HRMS of 4j

DQGWKH&HQWUH1DWLRQDOGHOD5HFKHUFKH6FLHQWLILTXH · Campus 43100 Kütahya, Turkey.. Corresponding...

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