Positional Effect of π-extension in Triple Helicenes

ChemRxiv

Abstract

Application of multiple helicenes in photo‐optical applications requires their rational design. We therefore here report on the synthesis of pyrene‐based triple helicene 1, to study the positional effect of extension of the π‐conjugated system on the photo‐chemical and chiro‐optical properties of triple helicenes. The conformational and aggregatory behavior of 1 were studied both experimentally using VT NMR spectroscopy and computationally using high‐level DFT computations. Although π‐extension was observed to have a marked effect on the spectroscopy properties of triple helicenes, comparison with other known π‐extended helicenes reveals that the position at which π‐extension is introduced is only of nominal importance. Our results thus suggest that the presence of a particular helicene motive is dominant in dictating the physico‐chemical properties of triple helicenes.

Authors 3

1. Hermen S. Overkleeft Aachen

   Leiden University

   Affiliation as printed

   Leiden University

2. Dmitri V. Filippov Aachen

   Leiden University

   Affiliation as printed

   Leiden University

3. Grégory F. Schneider Aachen

   Leiden University

   Affiliation as printed

   Leiden University