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

•(S)-Enantiomer of optically active metal free porphyrin was synthesized.•Chiral information transfer and expression at molecular and supramolecular level were studied.•LB films of the porphyrin were revealed to show good semiconductor features.

(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-hexaoxacycloeicosa-phenyl]-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 × 10−5 S m−1.

Graphical abstractThe appearance of induced CD signals indicates an effective chiral information transfer from the optically active binaphthyl moieties to the porphyrin chromophore in CHCl3. The bisignate Cotton effect is observed in the CD spectrum of the LB film, revealing the right-handed chirality formed in the LB film.Figure optionsDownload full-size imageDownload as PowerPoint slide