1640 (amide) 1588, 1573 (C]C aromatic), 1333 (C–N stretch),
806, 741 (CH aromatic). MS-ESI m/z ¼ 1333 [2M + Na]+.
1H NMR Spectroscopy
1
In each case of clicking the H NMR spectrum was measured.
The spectra are broadened as expected for a polymer. The
acetylene peak seen at 2.51 ppm in the scaffold is no longer
present and there is an additional peak at 7.60 ppm corre-
sponding to the proton of the triazole ring. This peak is very
evident in the samples in which the percentage of perylene is low,
however, as the quantity of perylene in the samples increases, the
aromatic region of the spectrum becomes broad and the triazole
peak is incorporated into the broad resonances for the perylene
11-Methoxy-3,6,9-trioxaundecyl p-toluenesulfonate 11
Tetraethylene glycol monomethyl ether (2.20 g, 10.57 mmol) and
triethylamine (1.62 mL, 11.62 mmol) were placed in a Schlenk
flask under nitrogen and dissolved in dichloromethane (50 mL).
The solution was cooled to 0 ꢁC and tosyl chloride (2.22 g, 11.62
mmol) in dichloromethane (60 mL) was added dropwise over 1
hour. The solution was left stirring overnight at room tempera-
ture after which time TLC showed residual tosyl chloride and the
desired product. The crude mixture was subject to column
chromatography; dichloromethane was used to elute the excess
tosyl chloride and 2% MeOH in CH2Cl2 to elute the desired
compound. The product was obtained as a colourless oil (2.55 g,
67%). Anal. Calcd for C16H26O7S: C, 53.02; H, 7.23. Found: C,
53.01; H, 7.42. 1H NMR (400 MHz, CDCl3, 20 ꢁC): d ¼ 2.44 (s, 3
H, CH3), 3.37 (s, 3 H, OCH3), 3.53–3.70 (overlapping multiplets,
1
protons. H NMR spectra of P1, P4 and P8 (in CDCl3) are
shown in Fig. S7, ESI‡.
IR spectroscopy
In each case of clicking the IR spectrum was measured. The peak
corresponding to the acetylene stretching frequency at 2129 cmꢂ1
is no longer evident and in addition no azide peaks can be seen
that would indicate unreacted azide in the sample.
3
14 H, CH2CH2OMe), 4.16 (t, 2 H, JHH ¼ 4.84 Hz, CH2OTS),
7.34 (d, 2 H, 3JHH ¼ 8.08 Hz, ArH ortho to OMe), 7.79 (d, 2 H,
3JHH ¼ 8.32 Hz, ArH ortho to OTs). 13C NMR (300 MHz,
Acknowledgements
ꢁ
The Technology Foundation STW, NanoNed, The Council for
the Chemical Sciences of the Netherlands Organisation for
Scientific Research, and the Royal Academy for Arts and
Sciences are acknowledged for financial support.
CDCl3, 20 C): d ¼ 21.6 (CH3), 59.0 (OCH3), 68.7, 69.2, 70.5,
70.5, 70.6, 70.6, 71.9 (CH2CH2), 128.0, 129.0 (ArC), 133.0
(CSO2), 144.8 (CCH3). FT-IR (cmꢂ1, ATR): 2870 (br, CH2/
CH3), 1175 (S]O).
References
1-Azido-11-methoxy-3,6,9-trioxaundecane 12
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ꢁ
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Typical procedure for random click reactions
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¨
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solvent removed to give the polymer as a solid. The polymers
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This journal is ª The Royal Society of Chemistry 2008
J. Mater. Chem., 2008, 18, 5615–5624 | 5623