Full Paper
d=0.92 (t, 9H, CH2CH2CH3), 1.32–1.43 (m, 18H, CH2(CH2)3CH2), 1.72
(quin, 6H, CH2CH2CS), 2.41 (quin, 6H, CH2CH2CH2), 2.79–2.87 (t, 6H,
CH2CH2CO, t, 6H, CH2CS), 4.50 (t, 6H, NCH2CH2), 6.75 (d, 3H,
CH2CCH), 7.05 (d, 3H, CH2CCHCH), 7.15 (d, 3H, CHCHCC-NI), 7.22 (d,
3H, CHCHCC-NI), 7.83–7.89 (t, 3H, CHCHCH, d, 3H, BT-CCH), 8.66
(d, 3H, BT-CCHCH), 8.76 (d, 3H, CHCHCH), 8.80 (d, 3H, CHCHCH),
9.17 ppm (s, 6H, CCHC); 13C NMR (75.5 MHz, CDCl3/[D1]TFA): d=
14.0, 22.6, 28.8, 30.2, 31.6, 120.0, 121.0, 122.5, 123.8, 124.4, 125.1,
126.2, 127.6, 128.2, 128.2, 129.2, 130.4, 130.4, 132.1, 133.0, 133.5,
136.1, 136.8, 137.5, 140.4, 141.5, 147.0, 165.5, 165.8, 175.2,
178.3 ppm; IR (neat): n˜ =3288 (w), 2925 (m), 2853 (m), 1695 (s),
1647 (s), 1585 (s), 1549 (m), 1463 (s), 1384 (m), 1348 (s), 1232 (m),
1156 (m), 1116 (m), 1051 (m), 857 (m), 801 cmꢀ1 (s); MALDI-TOF-
123.7, 124.1, 124.2, 125.1, 127.3, 128.2, 128.8, 128.9, 129.4, 129.9,
131.0, 131.7, 133.6, 137.3, 138.0, 139.1, 140.5, 146.6, 164.3, 164.6,
170.7 ppm; IR (neat): v˜ =3289 (m), 3062 (w), 2925 (s), 2854 (m),
1695 (s), 1652 (s), 1585 (s), 1534 (s), 1498 (m), 1438 (s), 1386 (s),
1350 (s), 1311 (w), 1249 (s), 1229 (s), 1174 (m), 1156 (m), 1119 (s),
1055 (s), 965 (m), 897 (s), 865 cmꢀ1 (s); MS: m/z calcd for
C36H34N2O3S2 [M]+ 606.20 gmolꢀ1, found 606 gmolꢀ1; thermally
stable up to 3008C, melting point: 1658C.
Acknowledgements
Financial support by the Bavarian State Ministry of Science, Re-
search, and the Arts for the Collaborative Research Network
“Solar Technologies go Hybrid” is gratefully acknowledged.
A.T.H., S.R.B., R.H., J.K., and H.W.S. are thankful for support by
the Deutsche Forschungsgemeinschaft (DFG) within GRK 1640.
A.T.H. would like to thank the elite study program “Macromo-
lecular Science” at the University of Bayreuth and the “Elite
Netzwerk Bayern” for a fellowship. M.K. and N.H. gratefully ac-
knowledge the support by the DFG as part of SFB953 “Synthet-
ic Carbon Allotropes”. We are indebted to Doris Hanft for syn-
thetic support and Dr. Klaus Kreger for many fruitful discus-
sions. We thank Prof. Dr. Anna Kçhler and Alexander Rudnick
for help with parts of the time-resolved measurements.
MS: m/z calcd for the Ag adduct
2016.43 gmolꢀ1, found 2016.47 gmolꢀ1
C
111H93AgN7O12S6 [M]+
.
Purification of compound 3: The crude product was boiled in di-
methylformamide for 2 h, cooled, filtered, and washed with water
and ethanol. The product was obtained as brown powder in 58%
1
yield (250 mg). H NMR (300.1 MHz, CDCl3/[D1]TFA): d=0.92 (t, 9H,
CH2 CH2CH3), 1.31–1.59 (m, 30H, CH2(CH2)5CH2), 1.94 (quin, 6H,
COCH2 CH2), 2.73 (t, 6H, COCH2), 8.99 ppm (s, 6H, CCHC); 13C NMR
(75.5 MHz, CDCl3/[D1]TFA): d=13.8, 22.7, 26.6, 29.2, 29.2, 29.3, 31.9,
37.5, 122.5, 127.1, 132.7, 137.0, 175.8, 178.5 ppm; IR (neat): n˜ =
3334 (m), 2921 (s), 2852 (s), 1703 (m), 1660 (m), 1633 (s), 1598 (s),
1548 (s), 1521 (m), 1358 (m), 1285 (m), 1258 (m), 1199 (m), 1158
(m), 1106 (m), 1017 (w), 910 (s), 869 (w), 801 cmꢀ1 (s); MS: m/z
calcd for C48H60N4O6 [M]+ 788.45 gmolꢀ1, found 788 gmolꢀ1; ther-
mally stable up to 3008C, melting was not observed below decom-
position temperature.
Keywords: bridged triarylamines · donor–acceptor molecules ·
General preparation method for the synthesis of the reference
compounds 4 and 5: The reactions of the acid chlorides 8 and 13
with aniline were conducted under argon and in dry conditions. In
a round-bottom flask, the respective acid chloride (1.0 equiv) was
dissolved in NMP, and aniline (2.5 equiv) was added as reactive
amine and as base. The mixture was stirred at 608C for 2 days.
energy transfer
compounds
· fluorescent gels · multichromophoric
Sagade, K. V. Rao, U. Mogera, S. J. George, A. Datta, G. U. Kulkarni, Adv.
Purification of compound 4: The reaction mixture was poured in
acidic (HCl) water. The precipitate was filtered off, washed with
water, and dried. The crude product was recrystallized from etha-
nol at 48C. The product was obtained as white powder in 79%
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1
yield (930 mg). H NMR (300.1 MHz, [D6]DSMO): d=2.30 (quin, 2H,
CH2CH2CH2), 2.72 (t, 2H, CH2CH2CO), 4.40 (t, 2H, NCH2CH2), 7.20–
7.39 (m, 5H, NH-C(CH)5), 7.84 (t, 2H, CHCHCH), 8.35 (d, 2H,
CHCHCH), 8.65 ppm (d, 2H, CHCHCH); 13C NMR (75.5 MHz, CDCl3/
[D1]TFA): d=24.1, 33.9, 40.3, 121.0, 122.2, 127.2, 127.7, 128.2, 129.4,
131.8, 133.3, 135.1, 136.5, 166.8, 175.5 ppm; IR (neat): v˜ =3279 (s),
3066 (w), 2959 (w), 1696 (s), 1654 (s), 1625 (m), 1590 (s), 1536 (s),
1499 (m), 1438 (s), 1386 (s), 1341 (s), 1246 (s), 1200 (m), 1168 (s),
1142 (m), 1047 (s), 971 (s), 894 (s), 846 cmꢀ1 (s); MS: m/z calcd for
, ; thermally
C22H18N2O3 [M]+ 358.13 gmolꢀ1 found 358 gmolꢀ1
stable up to 3008C, melting point: 2088C.
Purification of compound 5: The reaction mixture was poured in
acidic (HCl) water. The precipitate was filtered off, washed with
water, and dried. The crude product was recrystallized from etha-
nol at 48C. The product was obtained as orange powder in 58%
1
yield (290 mg). H NMR (300.1 MHz, [D6]DSMO): d=0.87 (t, 3H, CH2
CH2CH3), 1.23–1.37 (m, 6H, CH2(CH2)3CH2), 1.64 (quin, 2H,
CH2CH2CS), 2.02 (quin, 2H, CH2CH2CH2), 2.40 (t, 2H, CH2CH2CO),
2.81 (t, 2H, CH2CS), 4.17 (t, 2H, NCH2CH2), 6.88 (d, 1H, CH2CCH),
6.96 (d, 1H, CH2CCHCH), 7.19 (d, 1H, CHCHCC-NI), 7.27 (d, 1H,
CHCHCC-NI), 7.46 (m, 5H, NH-C(CH)5), 7.92 (t, 1H, CHCHCH), 7.94
(d, 1H, BT-CCH), 8.50 (d, 1H, BT-CCHCH), 8.57 ppm (d, 1H,
CHCHCH), 8.71 (d, 1H, CHCHCH); 13C NMR (75.5 MHz, [D2]TCE): d=
14.2, 22.5, 24.2, 28.7, 30.1, 31.4, 34.9, 39.5, 119.7, 121.0, 122.3,
[6] a) H. Imahori, T. Umeyama, K. Kurotobi, Y. Takano, Chem. Commun.
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Zandler, S. Fukuzumi, J. Am. Chem. Soc. 2012, 134, 654–664; d) ꢄ. J. Ji-
mꢅnez, R. M. K. Calderꢆn, M. S. Rodrꢃguez-Morgade, D. M. Guldi, T.
&
&
Chem. Eur. J. 2014, 20, 1 – 12
10
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