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.
Supplementary materials
Title
Positional Effect of π-extension in Triple Helicenes (Supplementary)
Description
Synthesis procedures, NMR spectra, computational methods, additional figures and tables, coordinates of computed structures.
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