Synthesis, spectroscopy, effective chiral information transfer and semiconducting property of optically active porphyrin derivative bearing four chiral binaphthyl moieties

(S)-Enantiomer of an optically active metal free porphyrin bearing four chiral binaphthyl units, namely (S)-meso-5,10,15,20-tetra-[(11,12: 13,14-di(6'-octyl-1',2'-naphtho)-4,7,10,15,18,21-hexaoxacycloeicosaphenyl]-porphyrin (1), was designed, synthesized, and characterized. Comparative studies of the circular dichroism (CD) spectra of (S)-1 in chloroform solution and LB film have been carried out, indicating the effective chiral information transfer from the optically active binaphthyl moieties to the porphyrin chromophore at the molecular level. In particular, obvious bisignate Cotton effect is observed in the CD spectrum of the LB film of (S)-1, revealing the right-handed chirality formed in the LB film. In addition, current-voltage (I-V) measurement result indicates good semiconductor feature of the LB film formed from (S)-1 with conductivity of 1.22 X 10(-5) S m(-)1. (C) 2014 Elsevier B.V. All rights reserved.