Synthesis and Photophysical Properties of a Sc₃N@C₈₀‐Corrole Electron Donor–Acceptor Conjugate

Abstract

Embedding endohdedral metallofullerenes (EMFs) into electron donor-acceptor systems is still a challenging task owing to their limited quantities and their still largely unexplored chemical properties. In this study, we have performed a 1,3-dipolar cycloaddition reaction of a corrole-based precursor with Sc3 N@C80 to regioselectively form a [5,6]-adduct (1). The successful attachment of the corrole moiety was confirmed by mass spectrometry. In the electronic ground state, absorption spectra suggest sizeable electronic communications between the electron acceptor and the electron donor. Moreover, the addition pattern occurring at a [5,6]-bond junction is firmly proven by NMR spectroscopy and electrochemical investigations performed with 1. In the electronically excited state, which is probed in photophysical assays with 1, a fast electron-transfer yields the radical ion pair state consisting of the one-electron-reduced Sc3 N@C80 and of the one-electron-oxidized corrole upon its exclusive photoexcitation. As such, our results shed new light on the practical work utilizing EMFs as building blocks in photovoltaics.

All‐Fullerene Electron Donor–Acceptor Conjugates

“…A wavelength of 387 nm was chosen to photoexcite 6 a / 6 b . In reference experiments with 4 (Figures S22–S25), its excited singlet state with its characteristic 495 and 580 nm maxima decayed within less than 100 ps, leading to the excited triplet state, in good agreement with earlier findings on TNTs . This state is characterized by a broad absorption, which maximizes at around 690 nm, and a slow filling of the ground state with (1.02±0.01)×10 6 s −1 .…”

Solvent dependent linear and nonlinear optical properties of triphenylamine unit incorporated difluoroboron β-diketonate complexes

“…Organic luminescent materials have gained extensive attention in recent decades for their wide applications in organic light emitting diodes (OLEDs) [1,2], mechano-chromic materials [3][4][5], chemical or biological sensing and imaging [6][7][8][9][10]. Among these, the organoboron luminogens [11][12][13] are particularly promising for their desirable photophysical and electronic properties, such as high carrier mobility, high molar absorption coefficients and high fluorescence quantum yields [14][15][16]. Their diverse reactivity profiles and high tolerance for structure modification create a great potential for applications of these molecules [17][18][19].…”

Ultrafast Photoinduced Charge Separation Leading to High‐Energy Radical Ion‐Pairs in Directly Linked Corrole–C60 and Triphenylamine–Corrole‐C60 Donor–Acceptor Conjugates

“…Owing to its resemblance to the natural photosynthetic chlorophyll pigment and relatively easy synthetic manipulations, porphyrin as the primary photoactive molecule has dominated this area of research . Its functions include panchromatic light harvesting through most of the visible part of the solar spectrum and electron transport.…”