Open-[60]fullerene–aniline conjugates with near-infrared absorption

(a) UV-vis-NIR absorption spectra of 1–3 (50 mM in benzene).

(b) Cyclic voltammograms of 1–3 (1 mM in ODCB, 0.1 M n-Bu4N$BF4,

100 mV s−1). (c) Molecular orbitals of 1–3 (B3LYP-D3/6-31G(d)).

Fig. 5

conjugates could be used for organic solar cells15a and perovskite solar cells.15b Upon seeing cyclic voltammograms (Fig. 5b),

the oxidation potentials Eox,pa of 2 (+0.44 V) and 3 (+0.26 V) were

cathodically shied by DE −0.92 and −1.10 V with respect to 1

(+1.36 V). This is in sharp contrast to the reduction potentials

without showing considerable shis. These observations

suggest that the conjugation with the aniline moiety renders the

HOMO levels higher while it has less contribution to the LUMO

levels. The oxidation wave found at Eox,pa −0.47 V might be

attributed to S-containing compounds16 partly decomposed

from 3 via electrochemical process. According to theoretical

calculations (B3LYP-D3/6-31G(d)), the LUMO delocalizes over

the entire [60]fullerene skeleton for all cases whereas high

HOMO coefficients were found at the N,N-dimethylaniline

moieties for 2 and 3 (Fig. 5c). Thus, the electrochemical

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