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14 The original sample was prepared in
October 2007 for single-crystal X-ray diffraction. The same sample
has been continuously exposed to atmospheric conditions; exposure to
light has not been continuous, but the sample has been in contact
with light for weeks at a time. The original ¹H
NMR is shown in the Supporting Information, as well as the ¹H NMR
taken from the same sample in October 2010 without performing any
purification. The October 2010 sample was simply dissolved in CDCl3 and
the spectrum was taken.
15 Into a thick-walled glass bomb (100
mL volume) were added 1,4-bis[(triisopropylsilyl)ethynyl]naphthalene-2,3-diamine (1; 0.400 g, 7.71 × 10-4 mol,
2 equiv) and 2,5-dihydroxy-benzoquinone (2;
0.054 g, 3.85 × 10-4 mol, 1 equiv),
which were dissolved in AcOH (30 mL). The reaction vessel was sealed
and heated to 120 ˚C for 6 d while stirring. The reaction
was cooled to r.t. and extracted with CH2Cl2 (50 mL).
The organic layer was washed with H2O (2 × 100
mL), dried with Na2SO4, and the solvent was
removed in vacuo. The crude mixture was purified by column chromatography on
silica gel using hexane-CH2Cl2 (3:1).
Compound 3 was isolated as a dark purple
solid (0.080 g, 18.7% yield); mp stable up to 400 ˚C.
IR (KBr): 3375, 3055, 2958, 2931, 2719, 2434, 2360, 2133, 1739,
1720, 1596, 1569, 1488, 1461, 1377, 1261, 1226, 1153, 1107 cm-¹. ¹H
NMR (CDCl3): δ = 8.60 (dd, J
1 = 3.3 Hz, J
2 = 6.7 Hz, 2 H),
7.94 (dd, J
1 = 3.2
Hz, J
2 = 6.2 Hz,
2 H), 7.62 (s, 2 H), 7.54 (dd, J
1 = 3.2
Hz, J
2 = 6.7 Hz,
2 H), 7.35 (dd, J
1 = 3.3
Hz, J
2 = 6.2 Hz,
2 H), 6.82 (s, 2 H), 1.29-1.30 (br m, 42 H), 1.25-1.26
(br m, 42 H). ¹³C NMR (CDCl3): δ = 145.7,
141.3, 135.8, 134.1, 130.9, 129.3, 127.3, 127.0, 126.0, 125.1, 119.1,
105.9, 105.7, 105.1, 103.4, 101.7, 99.5, 19.0, 18.9, 11.7, 11.4.
HRMS: m/z [M+] calcd
for C70H96N4Si4: 1104.6712;
found: 1104.6485.
