S1
SUPPORTING INFORMATION
New Poly(phenylenevinylene)-Methyl Methacrylate-Based
Photonic Crystals
Sylvain Achelle,1 Álvaro Blanco,2 Martín López-García,2 Riccardo Sapienza,2 Marta Ibisate,2
Cefe López,2 and Julián Rodríguez-López*,1
1
Facultad de Química, Universidad de Castilla-La Mancha, 13071-Ciudad Real, Spain. 2 Instituto de
Ciencia de Materiales de Madrid (CSIC), C/ Sor Juana Inés de la Cruz 3, 28049-Madrid, Spain
julian.rodriguez@uclm.es
Table of contents
1. General
S2
2. Experimental procedures and characterization data for compounds 2, 3, 5, 6, and 7.
S2-S7
3.
1
H NMR and 13C NMR spectra for dendritic iodides 2b-c.
S8–S11
4.
1
H NMR and 13C NMR spectra for dendritic aldehydes 5b-c and 6.
S12-S17
5.
1
H NMR and 13C NMR spectra for styrene derivatives 3a-c and 7.
S18-S25
S2
General. In air- and moisture-sensitive reactions all glassware was flame-dried and cooled under Ar.
THF was dried using a solvent purification system. Unless stated otherwise, NMR spectra were acquired
at 25 ºC. Chemical shifts are given in ppm relative to TMS (1H, 0.0 ppm) or CDCl3 (13C, 77.0 ppm). IR
spectra were recorded on an FT-IR spectrophotometer. UV/vis and fluorescence spectra were recorded
using standard 1 cm quartz cells. Compounds were excited at their absorption maxima (band of lowest
energy) for recording the emission spectra (uncorrected). MALDI mass spectra were registered using
dithranol as the matrix. Melting points are uncorrected.
Compounds 2a and 5a have been previously described.1 Dendritic aldehyde 5a can also be prepared
by reaction of the corresponding iodo derivative 2a with BunLi at –78 ºC, followed by quenching with
DMF.1
Synthesis of first generation aryl iodides 2. The synthesis was performed by Horner-WadsworthEmmons reaction of two molecules of the appropriate p-substituted benzaldehyde derivative with the
readily available diphosphonate 1.2
I
Me2N
NMe2
(E,E)-3,5-Bis(4-dimethylaminostyryl)iodobenzene (2b). Yield: 75% Yellow solid. Purified by
crystallization from CHCl3/EtOH. Mp 139.4-141.0 ºC. 1H-NMR (CDCl3, 500 MHz) : 2.99 (s, 12H,
4xCH3), 6.72 (A of ABq, 4H, J = 9.0 Hz, ArH), 6.80 (A of ABq, 2H, J = 16.0 Hz, 2xCH=), 7.04 (B of
ABq, 2H, J = 16.0 Hz, 2xCH=), 7.41 (B of ABq, 4H, J = 9.0 Hz, ArH), 7.46 (broad s, 1H, ArH), 7.64 (d,
2H, J = 1.0 Hz, ArH).
13
C-NMR, DEPT and g-HSQC (CDCl3, 125 MHz) : 40.4 (CH3), 95.2 (C1-I),
112.3 (m-CH), 122.6 (CH=), 123.2 (C4-H), 125.2 (ipso-C), 127.7 (o-CH), 130.0 (CH=), 132.7 (C2-H),
140.4 (C3), 150.3 (p-C). MALDI-TOF (dithranol) m/z 494.1 (M+). Anal. Calcd for C26H27IN2: C, 63.16;
H, 5.50; I, 25.67; N. 5.67. Found: C, 63.01; H, 5.52; N, 5.60.
1
(a) García-Martínez, J. C.; Atienza, C.; de la Peña, M.; Rodrigo, A. C.; Tejeda, J.; Rodríguez-López, J. J. Mass Spectrom.
2009, 44, 613-620. (b) Achelle, S.; Nouira, I.; Pfaffinger, B.; Ramondenc, Y.; Plé, N.; Rodríguez-López, J. J. Org. Chem.
2009, 74, 3711-3717. (c) Martín-Zarco, M.; Toribio, S.; García-Martínez, J.; Rodríguez-López J. Polym. Sci., Part A: Polym.
Chem. 2009, 47, 6409-6419.
2
Díez-Barra, E.; García-Martínez, J. C.; Rodríguez-López, J. J. Org. Chem. 2003, 68, 832-838.
S3
I
Ph2N
NPh2
(E,E)-3,5-Bis(4-diphenylaminostyryl)iodobenzene
(2c).
Purified
by
crystallization
from
CHCl3/EtOH. Yield: 78%. Yellow solid. Mp 197.6-198.4 ºC. 1H NMR (CDCl3, 500 MHz) : 6.88 (A of
ABq, 2H, J = 16.5 Hz, 2×CH=), 7.02-7.08 (m, 10H, 2×CH= and ArH), 7.10-7.13 (m, 8H, ArH), 7.247.29 (m, 8H, ArH), 7.38 (B of ABq, 4H, J = 8.5 Hz, ArH), 7.49 (broad s, 1H, ArH), 7.70 (d, 2H, J = 1.5
Hz, ArH).
13
C-NMR, DEPT and g-HSQC (CDCl3, 125 MHz) : 95.2 (C-I), 123.2 (CH), 123.3 (CH),
123.8 (C4-H), 124.7 (CH), 125.1 (CH=), 127.5 (CH), 129.3 (CH), 129.6 (CH), 130.7 (C), 133.5 (C2-H),
140.0 (C), 147.4 (C), 147.8 (C). MALDI-TOF (dithranol) m/z: 742.2 (M+). Anal. Calcd for C46H35IN2:
C, 74.39; H, 4.75; I, 17.09; N, 3.77. Found: C, 74.20; H, 4.70; N, 3.78.
General procedure for the synthesis of dendritic aldehydes 5 and 6 via Heck cross-coupling
reaction. A mixture of 3,5-dibromobenzaldehyde (1.00 g, 3.78 mmol), the appropriate styrene
derivative 4 (7.56 mmol, 3 for the synthesis of compound 6), anhydrous sodium carbonate (800 mg,
7.56 mmol), trans-di(µ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II)3 (7.69 mg, 8.19 µmol,
2,6-di-tert-butylcresol (419 mg, 1.89 mmol) and anhydrous N,N-dimethylacetamide (10 mL) was
deoxygenated thoroughly by stirring under vacuum followed by purging with argon several times. The
reaction mixture was then heated under argon at 130 °C for 24 h. After cooling, ethyl acetate (25 mL)
and 1M HCl (200 mL) were added carefully. The aqueous layer was extracted with ethyl acetate (3x25
mL). The combined organic layers were washed with water, dried (MsSO 4) and the solvent evaporated.
The crude product was purified by column chromatography over alumina (AcOEt/hexanes, 3/7)
followed by washing with hot ethanol.
CHO
Me2N
NMe2
(E,E)-3,5-Bis(4-dimethylaminostyryl)benzaldehyde (5b). Yield: 33%. Yellow solid. Mp 174.8176.1 ºC. 1H-NMR (CDCl3, 500 MHz) : 3.00 (s, 12H, 4xCH3), 6.74 (A of ABq, 4H, J = 9.0 Hz, ArH),
6.96 (A of ABq, 2H, J = 16.0 Hz, 2xCH=), 7.18 (B of ABq, 2H, J = 16.0 Hz, 2xCH=), 7.45 (B of ABq,
3
Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 13571364.
S4
4H, J = 9.0 Hz, ArH), 7.78 (t, 1H, J = 1.5 Hz, ArH), 7.81 (d, 2H, J = 1.5 Hz, ArH), 10.05 (s, 1H, CHO).
C-NMR (CDCl3, 125 MHz) : 40.4 (CH3), 112.4, 122.7, 125.0, 125.1, 127.8, 129.4, 130.5, 137.1,
13
139.4, 150.4, 192.8 (CHO). IR (ATR) : 1689 (C=O) cm–1. MALDI-TOF (dithranol) m/z 396.2 (M+·).
Anal. Calcd for C27H28N2O: C, 81.78; H, 7.12; N, 7.06. Found: C, 81.81; H, 7.10; N, 7.06.
CHO
Ph2N
NPh2
(E,E)-3,5-Bis(4-diphenylaminostyryl)benzaldehyde (5c).. Yield: 62%. Orange solid. Mp 114-116
ºC (CHCl3/EtOH). 1H NMR (CDCl3, 500 MHz) : 7.02-7.08 (m, 10H, 2×CH= and ArH), 7.11-7.14 (m,
8H, ArH), 7.19 (B of ABq, 2H, J = 16.0 Hz, 2×CH=), 7.25-7.29 (m, 8H, ArH), 7.41 (B of ABq, 4H, J =
9.0 Hz, ArH), 7.79 (broad s, 1H, ArH), 7.86 (d, 2H, J = 1.5 Hz, ArH), 10.06 (s, 1H, CH=O). 13C NMR
(CDCl3, 125 MHz) : 123.2, 123.3, 124.5, 124.7, 125.2, 125.7, 127.6, 129.3, 130.1, 130.6, 137.2, 139.0,
147.4, 147.9, 192.5 (CH=O). IR : 1693 (C=O) cm–1. MALDI-TOF (dithranol) m/z 644.2 (M+·). Anal.
Calcd for C47H36N2O: C, 87.55; H, 5.63; N, 4.34. Found: C, 87.77; H, 5.55; N, 4.30.
C6H13O
CHO
OC6H13
OC6H13
OC6H13
(E,E,E,E,E,E)-3,5-Bis[3,5-bis(4-hexyloxystyryl)styryl]benzaldehyde (6). Yield: 92%. Pale yellow
solid. Mp 192.4-194.6 ºC. 1H NMR (CDCl3, 500 MHz) : 0.92 (t, 12H, J = 7.0 Hz, 4×CH3), 1.36 (m,
16H, 8×CH2), 1.48 (m, 8H, 4×CH2), 1.80 (m, 8H, 4×CH2), 3.99 (t, 8H, J = 6.5 Hz, 4×OCH2), 6.91 (A of
ABq, 8H, J = 8.5 Hz, ArH), 6.99 (A of ABq, 4H, J = 16.5 Hz, 4×CH=), 7.14 (B of ABq, 4H, J = 16.5 Hz,
4×CH=), 7.21 (A of ABq, 2H, J = 16.0 Hz, 2×CH=), 7.26 (B of ABq, 2H, J = 16.0 Hz, 2×CH=), 7.47 (B
of ABq, 8H, J = 8.5 Hz, ArH), 7.51 (broad s, 6H, ArH), 7.87 (broad s, 1H, ArH), 7.91 (d, 2H, J = 1.5
Hz, ArH), 10.06 (s, 1H, CH=O).
13
C NMR and DEPT (CDCl3, 125 MHz) : 14.0 (CH3), 22.6 (CH2),
25.7 (CH2), 29.3 (CH2), 31.6 (CH2), 68.1 (OCH2), 114.8 (CH), 123.4 (CH), 124.1 (CH), 126.0 (CH),
126.4 (CH), 127.3 (CH), 127.8 (CH), 129.0 (CH), 129.8 (C), 130.2 (CH), 130.6 (CH), 137.2 (C), 138.5
S5
(C), 138.7 (C), 159.1 (C), 192.2 (CH=O). IR : 1697 (C=O) cm–1. MALDI-TOF (dithranol) m/z: 1119.3
(M+), 1120.3 (M++1). Anal. Calcd for C79H90O5: C, 84.75; H, 8.10. Found: C, 84.99; H, 8.01.
General procedure for the synthesis of dendritic styrene derivatives 3 via Suzuki cross-coupling
reaction reaction. To a suspension of potassium vinyltrifluoroborate (670 mg, 5 mmol), cesium
carbonate (4.89 g, 15.0 mmol), PdCl2(dppf)CH2Cl2 (368 mg, 0.44 mmol) and the appropriate iodo
derivative 2 (3,33 mmol) in THF (60 mL) was added degassed water (6 mL) followed by heating at
reflux. The reaction mixture was stirred at reflux for 6 h, then cooled to room temperature and diluted
with water (50 mL). The THF was evaporated under vacuum and the aqueous layer was extracted with
dichloromethane (3x50 mL). The organic layers were combined, washed with 1 M HCl (50 mL), brine
(50 mL) and dried (MgSO4). The solvent was removed under vacuum and the crude product was
purified by alumina column chromatography (AcOEt/hexanes, 3/7) followed by washing with hot
ethanol
General procedure for the synthesis of dendritic styrene derivatives 3 and 7 via Wittig reaction:
Potassium tert-butoxide (1.23 g, 11.0 mmol) was added to a solution of methyltriphenylphosphonium
iodide (5.07 g, 10 mmol) in dry THF (60 mL), and the reaction mixture was stirred at room temperature
for 15 min. The appropriate aldehyde 2 (6.67 mmol, 6 for the synthesis of compound 7) was added and
the reaction mixture was stirred at room temperature for 90 min. The reaction was hydrolyzed with
water (50 mL), and the THF was removed under vacuum. The aqueous layer was extracted with CH2Cl2
(3x50 mL), and the combined organic layers were dried (MgSO4) and evaporated. The crude product
was filtered through a plug of alumina using dichloromethane as eluent. The filtrate was collected and
the solvent completely removed. The solid obtained was washed with hot ethanol.
C6H13O
OC6H13
(E,E)-3,5-Bis(4-hexyloxystyryl)styrene (3a).. Yield: 87%. Pale yellow solid. Mp 102.8-104.3 ºC.
1
H-NMR (CDCl3, 500 MHz) : 0.91 (t, 6H, J = 7.0 Hz, 2×CH3), 1.35 (m, 8H, 4×CH2), 1.47 (m, 4H,
2×CH2), 1.79 (m, 4H, 2×CH2), 3.98 (t, 4H, J = 6.5 Hz), 5.30 (d, 1H, J = 11.0 Hz, CH=), 5.83 (d, 1H, J =
17.5 Hz, CH=), 6.76 (dd, 1H, J = 17.5 Hz, J = 11.0 Hz, CH=), 6.90 (A of ABq, 4H, J = 8.5 Hz, ArH),
6.99 (A of ABq, 2H, J = 16.5 Hz, 2×CH=), 7.12 (B of ABq, 2H, J = 16.5 Hz, 2×CH=), 7.40 (d, 2H, J =
S6
1.5 Hz, ArH), 7.46 (B of ABq, 4H, J = 8.5 Hz, ArH), 7.51 (broad s, 1H, ArH).
13
C-NMR and DEPT
(CDCl3, 125 MHz) : 14.0 (CH3), 22.6 (CH2), 25.7 (CH2), 29.2 (CH2), 31.6 (CH2), 68.1 (OCH2), 114.2
(CH2), 114.7 (CH), 123.0 (CH), 123.6 (CH), 126.2 (CH), 127.7 (CH), 128.7 (CH), 129.8 (C), 136.8
(CH), 138.1 (C), 138.2 (C). IR (ATR) : 1604, 1582, 1574, 1510, 1250, 1172 cm–1. MALDI-TOF
(dithranol) m/z 508.3 (M+·). Anal. Calcd for C36H44O2: C, 84.99; H, 8.72. Found: C, 84.85; H, 8.62.
Me2N
NMe2
(E,E)-3,5-Bis(4-dimethylaminostyryl)styrene (3b).. Yield: 76%. Pale yellow solid. Mp 129.3-130.9
ºC. 1H-NMR (CDCl3, 500 MHz) : 2.99 (s, 12H, 4xCH3), 5.28 (dd, 1H, J = 11.0 Hz, J = 1.0 Hz, CH=),
5.82 (dd, 1H, J = 18.0 Hz, J = 1.0 Hz, CH=), 6.72-6.78 (m, 5H, CH= and ArH), 6.93 (A of ABq, 2H, J =
16.0 Hz, 2xCH=), 7.10 (B of ABq, 2H, J = 16.0 Hz, 2xCH=), 7.37 (d, 2H, J = 1.5 Hz, ArH), 7.44 (B of
ABq, 4H, J = 9.0 Hz, ArH), 7.49 (broad s, 2H, ArH). 13C-NMR, DEPT and g-HSQC (CDCl3, 125 MHz)
: 40.5 (CH3), 112.4 (CH), 113.9 (CH2), 122.4 (CH), 123.2 (CH), 124.2 (CH), 125.7 (C), 127.6 (CH),
129.0 (CH), 137.0 (CH), 138.0 (C), 138.5 (C), 150.1 (C). IR (ATR) : 1601, 1580, 1520, 1356 cm–1.
MALDI-TOF (dithranol) m/z 394.2 (M+·). Anal. Calcd for C28H30N2: C, 85.24; H, 7.66; N, 7.10. Found:
C, 85.00; H, 7.59; N, 7.14.
Ph2N
NPh2
(E,E)-3,5-Bis(4-diphenylaminostyryl)styrene (3c). Yield: 76%. Yellow solid. Mp 106-107.5 ºC. 1HNMR (CDCl3, 500 MHz) : 5.31 (d, 1H, J = 11.5 Hz, CH=), 5.83 (d, 1H, J = 17.5 Hz, CH=), 6.76 (dd,
1H, J = 17.5 Hz, J = 11.5 Hz, CH=), 7.01 (A of ABq, 2H, J = 16.5 Hz, 2×CH=), 7.01-7.08 (m, 8H,
ArH), 7.10-7.13 (m, 10H, 2×CH= and ArH), 7.25-7.29 (m, 8H, ArH), 7.41 (B of ABq, 4H, J = 8.5 Hz,
ArH), 7.41 (broad s, 2H, ArH), 7.51 (broad s, 1H, ArH).
13
C-NMR (CDCl3, 125 MHz) : 114.3, 123.1,
123.2, 123.5, 123.7, 124.5, 126.7, 127.4, 128.6, 129.3, 131.3, 136.7, 138.2, 138.2, 147.4, 147.5.
MALDI-TOF (dithranol) m/z 642.3 (M+·). Anal. Calcd for C48H38N2: C, 89.68; H, 5.96; N, 4.36. Found:
C, 89.83; H, 6.11; N, 4.25.
S7
C6H13O
OC6H13
C80H92O4
Exact Mass: 1116,6996
Mol. Wt.: 1117,5841
C, 85,98; H, 8,30; O, 5,73
OC6H13
OC6H13
(E,E,E,E,E,E)-3,5-Bis[3,5-bis(4-hexyloxystyryl)styryl]styrene (7). Yield: 51%. Pale yellow solid.
Mp 135.9-135.7 ºC. 1H NMR (CDCl3, 500 MHz) : 0.92 (t, 12H, J = 7.0 Hz, 4×CH3), 1.35 (m, 16H,
8×CH2), 1.48 (m, 8H, 4×CH2), 1.80 (m, 8H, 4×CH2), 3.98 (t, 8H, J = 6.5 Hz, 4×OCH2), 5.35 (d, 1H, J =
11.0 Hz, CH=), 5.88 (d, 1H, J = 17.5 Hz, CH=), 6.80 (dd, 1H, J = 17.5 Hz, J = 11.0 Hz, CH=), 6.91 (A
of ABq, 8H, J = 9.0 Hz, ArH), 7.01 (A of ABq, 4H, J = 16.5 Hz, 4×CH=), 7.15 (B of ABq, 4H, J = 16.5
Hz, 4×CH=), 7.21 (s, 4H, 4×CH=), 7.48 (B of ABq, 8H, J = 9.0 Hz, ArH), 7.49 (s, 2H, ArH), 7.50 (s,
2H, ArH), 7.53 (s, 4H, ArH), 7.63 (broad s, 1H, ArH). 13C NMR and DEPT (CDCl3, 125 MHz) : 14.0
(CH3), 22.6 (CH2), 25.7 (CH2), 29.2 (CH2), 31.6 (CH2), 68.1 (OCH2), 114.5 (CH2), 114.7 (CH), 123.3
(CH), 123.7 (CH), 123.9 (CH), 124.1 (CH), 126.1 (CH), 127.8 (CH), 128.6 (CH), 128.8 (CH), 129.1
(CH), 129.8 (C), 136.6 (CH), 137.8 (C), 137.9 (C), 138.3 (C), 138.4 (C), 159.0 (C). IR : 1607, 1585,
1508, 1246, 1172, 954 cm–1. MALDI-TOF (dithranol) m/z: 1117.3 (M+), 1118.3 (M++1). Anal. Calcd
for C80H92O4: C, 85.98; H, 8.30. Found: C, 86.28; H, 8.24.
S8
2.99
I
Me2N
NMe2
2b
Solvent: CDCl3
500 MHz
7.6
7.4
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0
S9
I
Me2N
127.7
NMe2
2b
Solvent: CDCl3
125 MHz
112.3
40.4
132.7
130.0
122.6
140.4
123.2
150.3
150
95.2
125.2
140
130
120
110
100
90
80
70
60
50
40
S10
I
Ph2N
NPh2
2c
Solvent: CDCl3
500 MHz
7.70
7.60
7.50
7.40
7.30
7.20
7.10
7.00
6.90
6.80
S11
I
Ph2N
2c
NPh2
Solvent: CDCl3
125 MHz
147.4
133.5
147.8
95.2
140.0
140
130
120
110
100
S12
3.00
CHO
Me2N
5b
NMe2
Solvent: CDCl3
500 MHz
7.80
7.60
7.40
7.20
7.00
6.80
10.05
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
S13
CHO
Me2N
NMe2
5b
Solvent: CDCl3
125 MHz
125.40
125.20
125.00
124.80
124.60
40.4
192.8
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
S14
CHO
Ph2N
5c
NPh2
Solvent: CDCl3
500 MHz
10.06
10.2
10.0
9.8
9.6
9.4
9.2
9.0
8.8
8.6
8.4
8.2
8.0
7.8
7.6
7.4
7.2
7.0
S15
CHO
Ph2N
NPh2
5c
Solvent: CDCl3
125 MHz
192.5
190
180
170
160
150
140
130
120
S16
C6H13O
CHO
OC6H13
OC6H13
OC6H13
6
Solvent: CDCl3
125 MHz
7.80
7.60
7.40
7.20
7.00
10.06
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
S17
C6H13O
CHO
OC6H13
OC6H13
OC6H13
6
Solvent: CDCl3
125 MHz
14.0
114.8
68.1
159.1
192.2
190
180
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
S18
C6H13O
OC6H13
3a
Solvent: CDCl3
500 MHz
7.50
7.5
7.0
7.40
6.5
7.30
7.20
6.0
7.10
5.5
7.00
6.90
5.0
6.80
4.5
6.70
4.0
3.5
3.0
2.5
2.0
1.5
1.0
S19
C 6H 13O
OC 6 H 13
3a
Solvent: CDCl3
125 MHz
130 129 128 127 126 125 124 123 122 121 120 119 118 117 116 115 114 113
14.0
68.1
159.0
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
S20
Me2N
NMe2
3b
Solvent: CDCl3
500 MHz
7.50
7.6
7.4
7.2
7.40
7.0
7.30
6.8
7.20
6.6
7.10
6.4
7.00
6.90
6.2
6.80
6.0
6.70
5.8
5.6
5.4
5.2
5.0
4.8
4.6
4.4
4.2
4.0
3.8
3.6
3.4
3.2
3.0
S21
Me2N
NMe2
3b
Solvent: CDCl3
125 MHz
127.6
112.4
40.5
113.9
150.1
150
140
130
120
110
100
90
80
70
60
50
40
S22
Ph2N
NPh2
3c
Solvent: CDCl3
500 MHz
7.4
7.2
7.0
6.8
6.6
6.4
6.2
6.0
5.8
5.6
5.4
S23
Ph2N
NPh2
3c
Solvent: CDCl3
125 MHz
129.3
124.5
147.5
138.2
147.4
138.2
114.3
148
146
144
142
140
138
136
134
132
130
128
126
124
122
120
118
116
114
S24
C6H13O
OC6H13
OC6H13
OC6H13
7
Solvent: CDCl3
500 MHz
7.60
7.5
7.40
7.0
7.20
6.5
6.0
7.00
5.5
6.80
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
S25
114.7
C6H13O
127.8
OC6H13
OC6H13
OC6H13
7
114.5
138
136
134
132
130
128
126
124
122
120
118
116
Solvent: CDCl3
125 MHz
114
68.1
14.0
159.0
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20