Degradation-assisted doping of organic semiconductors enabled by Lewis acids (nature.com)

a) Electron transfer between P3HT (illustrated as a three-repeat-unit segment) and BCF. b) The BCF radical anion undergoes degradation and first forms a singly-chlorinated degradation product [Cl-B(C6F5)3]− by interacting with chloroform (the solvent), which occurs rapidly as deduced from NMR spectroscopy (Fig. 3 in the Main Text). Following this, slower degradation pathways emerge in the system and enable the generation of the doubly-chlorinated degradation product [Cl2-B(C6F5)2]−, equally observed in NMR at later time points. We note that the dichloromethyl radical generated after chlorine abstraction from the solvent can recombine very fast into multiple non-assignable products, including notably with another dichloromethyl radical, as well as with the perfluorinated ring liberated and forming [Cl2-B(C6F5)2]−. Therefore, the resulting mixture of products is complex, and includes [B(C6F5)4-nCln]− for n = 1 and n = 2, corresponding to the main products, as well as the dichloromethyl (CCl2H) radical, which recombines or further degrades in a variety of pathways and thus produces numerous species represented by CHxCly(C6F5)z, where the central carbon of chloroform is now bound to a different numbers of hydrogen(s), chlorine(s), and perfluorohpenyl ring(s) such that x + y + z = 4. We stress that although there exists a number of unresolved species...