Issue 38, 2022

Dithia[9]helicenes: Molecular design, surface imaging, and circularly polarized luminescence with enhanced dissymmetry factors

Abstract

Synthesis of two dithia[9]helicenes by means of a LED-based double photocyclization is reported. The compounds have sulfur atoms placed at the terminal rings of the helicene, and they display two alternative C2-symmetrical arrangements named exo (1) and endo (2). Separation of enantiomers of opposite helicity allowed the complete characterization in solution, in silico, by X-ray crystallography, and adsorbed on gold. The theoretical analysis confirms the unexpected finding that endo-dithia[9]helicene displays an experimental dissymmetry factor (glum) in CPL larger than its isomer exo-dithia[9]helicene (–0.0125 vs. −0.0042). This enhanced glum factor ranks among the largest for a helicene-type molecule. Comparison with smaller analogues, namely exo and endo-dithia[7]helicenes (10 and 11, respectively), is also presented.

Graphical abstract: Dithia[9]helicenes: Molecular design, surface imaging, and circularly polarized luminescence with enhanced dissymmetry factors

Supplementary files

Article information

Article type
Paper
Submitted
11 7 2022
Accepted
03 9 2022
First published
05 9 2022
This article is Open Access
Creative Commons BY-NC license

J. Mater. Chem. C, 2022,10, 14306-14318

Dithia[9]helicenes: Molecular design, surface imaging, and circularly polarized luminescence with enhanced dissymmetry factors

B. C. Baciu, P. J. Bronk, T. de Ara, R. Rodriguez, P. Morgante, N. Vanthuyne, C. Sabater, C. Untiedt, J. Autschbach, J. Crassous and A. Guijarro, J. Mater. Chem. C, 2022, 10, 14306 DOI: 10.1039/D2TC02910C

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