Molecules 2021, 26, 2378
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15.73, 13.53. MS (rel. int., %) m/z: 524 (M+, 2.3), 436 (23.0), 281 (10.3), 207 (22.9), 44 (100.0).
HRMS (APCI-QTOF) calculated mass for C24H28O3Se2 [M]+: 524.0368, found: 524.0363.
3-(Butylselanyl)-4-methoxy-2,5-bis(4-methoxyphenyl)selenophene 4g: Yield: 0.051
1
g (40%); yellow oil. H NMR (CDCl3, 400 MHz)
δ
(ppm) = 7.63 (d, J = 8.6 Hz, 2H); 7.50 (d,
J = 8.6 Hz, 2H); 6.97–6.91 (m, 4H); 3.85 (s, 3H); 3.84 (s, 3H); 3.76 (s, 3H); 2.74 (t, J = 7.4 Hz,
2H); 1.50 (quint, 7.4 Hz, 2H); 1.31–1.24 (m, 2H); 0.80 (t, J = 7.4 Hz, 3H). 13C NMR (CDCl3,
100 MHz)
δ (ppm) = 159.42, 158.84, 154.04, 144.57, 130.94, 130.62, 129.35, 129.06, 127.09,
118.78, 114.11, 113.62, 60.60, 55.30 (2C), 32.17, 27.94, 22.69, 13.51. MS (rel. int., %) m/z:
510 (M+, 8.3), 207 (55.7), 73 (86.2), 44 (100.0). HRMS (APCI-QTOF) calculated mass for
C23H26O3Se2 [M]+: 510.0212, found: 510.0220.
3-(Butylselanyl)-4-ethoxy-2,5-di-4-tolylselenophene 4h: Yield: 0.098 g (80%); yellow
1
oil. H NMR (CDCl3, 400 MHz)
δ
(ppm) = 7.60 (d, J = 8.0 Hz, 2H); 7.46 (d, J = 8.0 Hz, 2H);
7.19 (t, J = 8.7 Hz, 4H); 3.98 (q, J = 7.0 Hz, 2H); 2.78 (t, J = 7.4 Hz, 2H); 2.38 (s, 3H); 2.36
(s, 3H); 1.51 (quint, J = 7.4 Hz, 2H); 1.33 (t, J = 7 Hz, 3H); 1.26 (sext, J = 7.4 Hz, 2H); 0.81
(t, J = 7.4 Hz, 3H). 13C NMR (CDCl3, 100 MHz)
δ
(ppm) = 153.70, 145.05, 137.82, 136.98,
134.04, 131.84, 129.32, 129.28, 128.89, 127.72, 127.68, 119.58, 69.03, 32.17, 27.87, 22.70, 21.27,
21.21, 15.74, 13.51. 77Se NMR (CDCl3, 76 MHz)
δ (ppm) = 578.7, 198.5. MS (rel. int., %) m/z:
492 (M+, 89.4), 246 (62.0), 207 (48.2), 183 (100.0), 91 (27.7), 44 (27.9). HRMS (APCI-QTOF)
calculated mass for C24H29OSe2 [M + H]+: 493.0548, found: 493.0539.
3-(Butylselanyl)-4-ethoxy-2,5-di-2-tolylselenophene 4m: Yield: 0.018 g (15%); yel-
1
low oil. H NMR (CDCl3, 400 MHz)
δ
(ppm) = 7.42 (d, J = 7.3 Hz, 1H); 7.29–7.26 (m, 4H);
7.23–7.20 (m, 3H); 3.76 (q, J = 7.0 Hz, 2H); 2.69 (t, J = 7.4 Hz, 2H); 2.37 (s, 3H); 2.31 (s, 3H);
1.47 (quint, J = 7.4 Hz, 2H); 1.31–1.21 (m, 2H); 1.14 (t, J = 7.0 Hz, 3H); 0.82 (t, J = 7.4 Hz, 3H).
13C NMR (CDCl3, 100 MHz)
δ (ppm) = 145.28, 137.67, 137.11, 136.51, 134.07, 130.96, 130.69,
130.07, 129.92, 128.34, 127.96, 125.41, 125.17, 119.99, 68.96, 32.35, 29.70, 26.97, 22.73, 20.49,
20.46, 15.56, 13.54. MS (rel. int., %) m/z: 492 (M+, 87.4), 246 (94.4), 207 (93.9), 183 (58.5),
91 (41.9), 44 (100.0). HRMS (APCI-QTOF) calculated mass for C24H28OSe2 [M]+: 492.0470,
found: 492.0477.
3-(Butylselanyl)-4-methoxy-2,5-di-2-tolylselenophene 4n: Yield: 0.030 g (25%); yel-
1
low oil. H NMR (CDCl3, 400 MHz)
δ
(ppm) = 7.44 (d, J = 7.2 Hz, 1H); 7.29–7.21 (m, 7H);
3.56 (s, 3H); 2.67 (t, J = 7.3 Hz, 2H); 2.36 (s, 3H); 2.31 (s, 3H); 1.49 (quint, J = 7.3 Hz, 2H);
1.29–1.22 (m, 2H); 0.82 (t, J = 7.3 Hz, 3H). 13C NMR (CDCl3, 100 MHz)
δ
(ppm) = 153.39,
145.68, 137.76, 137.09, 136.39, 133.94, 130.97, 130.70, 130.07, 129.93, 128.38, 128.09, 127.08,
125.45, 125.17, 119.40, 60.66, 32.36, 27.07, 22.71, 20.50, 20.39, 13.53. 77Se NMR (CDCl3,
76 MHz) δ
(ppm) = 617.2, 210.3. MS (rel. int., %) m/z: 478 (M+, 84.8), 416 (9.0), 341 (37.6),
310 (9.4), 143 (100.0), 115 (88.7), 91 (55.7), 44 (67.6). HRMS (APCI-QTOF) calculated mass
for C23H27OSe2 [M + H]+: 479.0391, found: 479.0388.
3-(Butylselanyl)-2,5-bis(2-chlorophenyl)-4-ethoxyselenophene 4o: Yield (determined
by 1H NMR): 15%; yellow oil. Mixture of compounds 4m and diyne 1i (ratio 69:31%). Asterisk
denotes the chemical shifts of the diyne 1i. 1H NMR (CDCl3, 400 MHz)
δ (ppm) = 7.63–7.61
(m, 1H); 7.57* (d, J = 7.4 Hz, 2H); 7.47 (d, J = 6.4 Hz, 2H); 7.42* (d, J = 7.4 Hz, 2H); 7.32–7.29 (m,
5H), 7.26–7.22* (m, 2H); 3.87 (q, J = 7.0 Hz, 2H); 2.75 (t, J = 7.3 Hz, 2H); 1.51 (quint, J = 7.3 Hz,
2H); 1.31–1.22 (m, 2H); 1.18 (t, J = 7.0 Hz, 3H); 0.82 (t, J = 7.3 Hz, 3H). 13C NMR (CDCl3,
100 MHz)
δ (ppm) = 154.35, 143.72, 136.95*, 135.77, 134.36*, 134.09, 133.98, 133.43, 132.57,
132.41, 130.28*, 129.76, 129.56, 129.44*, 129.15, 126.54*, 126.46, 126.22, 121.80*, 121.34, 79.40*,
78.37*, 69.23, 32.23, 27.29, 22.69, 15.54, 13.53. 77Se NMR (CDCl3, 76 MHz)
δ (ppm) = 623.1,
208.5. MS (rel. Int.) m/z: 532 (M+; 13.2), 441 (14.3), 203 (58.8), 123 (17.9), 41 (100.0). HRMS
(APCI-QTOF) calculated mass for C22H23Cl2OSe2 [M + H]+: 532.9446, found: 532.9438.
3-(Butylselanyl)-2,5-bis(2-chlorophenyl)-4-methoxyselenophene 4p: Yield: 0.032 g
1
(25%); yellow oil. H NMR (CDCl3, 400 MHz)
δ
(ppm) = 7.63–7.57 (m, 1H); 7.49–7.46 (m,
2H); 7.43–7.40 (m, 1H); 7.35–7.29 (m, 4H); 3.66 (s, 3H); 2.74 (t, J = 7.4 Hz, 2H); 1.51 (quint,
J = 7.4 Hz, 2H); 1.31–1.22 (m, 2H); 0.82 (t, J = 7.4 Hz, 3H). 13C NMR (CDCl3, 100 MHz)
δ
(ppm) = 154.89, 144.03, 135.67, 134.36, 134.08, 133.34, 132.54, 132.44, 130.27, 129.77, 129.59,
129.30, 126.52, 126.23, 125.06, 120.82, 60.77, 32.25, 27.39, 22.69, 13.53. 77Se NMR (CDCl3,