Intramolecular charge-transfer interaction in a new dyad based on C(60) and bis(4'-tert-butylbiphenyl-4-yl)aniline (BBA) donor

T Ohno; K Moriwaki; T Miyata

doi:10.1021/jo001100q

Intramolecular charge-transfer interaction in a new dyad based on C(60) and bis(4'-tert-butylbiphenyl-4-yl)aniline (BBA) donor

J Org Chem. 2001 May 18;66(10):3397-401. doi: 10.1021/jo001100q.

Authors

T Ohno¹, K Moriwaki, T Miyata

Affiliation

¹ Osaka Municipal Technical Research Institute, 1-6-50 Morinomiya, Joto-ku, Osaka 536-8553, Japan. ohno@omtri.city.osaka.jp

PMID: 11348122
DOI: 10.1021/jo001100q

Abstract

A novel dyad 2 based on C(60) and bis(4'-tert-butylbiphenyl-4-yl)aniline (BBA) donor has been synthesized and characterized. Cyclic voltammetry (CV) and UV-vis spectra of 2, 61-phenyl-1, 2-methanofullerene[60] 4, 1,2-methanofullerene[60] 5, and BBA were measured and analyzed. CV measurements showed that a reversible oxidation wave of 2 was positively shifted by 40 mV compared to that of BBA. More remarkably, comparing UV-vis spectra of 2 and 5 shows the big hyperchromic effect of 2 on a broad band at 500 nm despite lacking of more than 400 nm of absorbance for BBA. These results indicate obvious evidence of intramolecular charge-transfer interactions between C(60)-moiety and BBA.