The light-induced charge-transfer (CT) state in the composite of the conductive polymer poly(3-hexylthiophene) (P3HT) and the fullerene derivative [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) has been studied by electron spin echo (ESE) spectroscopy. The out-of-phase ESE signal corresponding to the spin-correlated radical pair P3HT(+)/PCBM(-) has been observed in this composite material. The time-domain ESE shape for different delays between the laser flash and the microwave pulse sequence has been analyzed. In order to explain the evolution of the out-of-phase ESE signal as a function of the delay between the microwave pulses, a model of the CT state is proposed. The hole is assumed to be delocalized on the P3HT chain over several thiophene subunits, while the point-dipole approximation is used to describe the interaction with the electron on PCBM. The distribution of distances between the positive and negative charges in the CT state has been evaluated.
A composite of conductive polythiophene P3HT and soluble fullerene derivative PC 70 BM (the material widely used as the active layer in organic photovoltaics devices) was studied by light-induced EPR (LEPR). In contrast to P3HT/PC 60 BM composite, LEPR signal in P3HT/PC 70 BM can be detected in a wide temperature range up to room temperature. This signal was attributed to charge carriers P3HT + and PC 70 BM − . The dependence of the intensity of LEPR signal on light intensity and the decay of LEPR signal upon switching light off are interpreted in frame of trap-limited bimolecular recombination model with finite rate of back electron transfer in [P3HT + PC 70 BM − ] encounter complex at polymer−fullerene interface. The apparent recombination order was found to be close to p = 3.5 for the temperature range from 100 K to room temperature. For temperatures above 150 K Arrhenius behavior of effective recombination rate constant was obtained with the activation energy E a = 0.16 ± 0.01 eV, which is larger than analogous values for P3HT/PC 60 BM reported previously. This difference is attributed to the change of polymer/fullerene interface induced by the replacement of PC 60 BM by PC 70 BM.
A general and effective method for the synthesis of 3‐phenylveradzyl radicals bearing a variety of iodophenyl substituents has been developed. The synthesized radicals have been characterized by ESR, UV/Vis spectroscopy, and cyclic voltammetry. Structures of biphenyl‐substituted radicals have been solved by X‐ray crystal structure analysis. The synthesized iodoverdazyls are applicable in the Sonogashira coupling reaction for the preparation of a wide range of ethynyl derivatives. Both N‐2 and C‐6 substituents were functionalized through Sonogashira coupling.
A novel approach to the preparation of stable Pd-substituted verdazyls was developed through the direct oxidative addition of iodoverdazyls to Pd(PPh3)4.
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