Electronic and steric effects controlling efficiencies of photoaddition reactions of fullerene C60 with N-α-trimethylsilyl-N-alkyl-N-benzylamines

Add time:08/29/2019    Source:sciencedirect.com

Single electron transfer (SET)-promoted photoaddition reactions between fullerene C60 and both various alkyl (Me, Et, i-Pr, t-Bu)- and para-substituted (p-Me, p-OMe, p-F, p-CF3) arene ring containing, N-α-trimethylsilyl-N-alkyl-N-benzylamines were explored to gain information about photoproduct profiles and how the electronic and steric nature of the amine substrates influence reaction efficiencies. The results show that visible light (λ > 540 nm) irradiation of 10% EtOH-toluene solutions containing C60 and N-α-trimethylsilyl-N-alkyl-N-benzylamines produce 1-aminomethyl-1,2-dihydrofullerenes as a sole photoproduct. In addition, SET-promoted photoaddition reactions of unsubstituted and para-electron donating group substituted arene ring containing N-α-trimethylsilyl-N-alkyl-N-benzylamines take place to give photoproducts more efficiently than those containing para-electron withdrawing group substituted arene rings. Moreover, although steric factors are less significant than the electronic nature of the amine substrates in governing reaction efficiencies, sterics do play a significant role in photoreactions of electron deficient amine substrates.

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