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Straightforward Synthesis and Properties of Highly Fluorescent [5]‐ and [7]‐Helical Dispiroindeno[2,1‐ c ]fluorenes
Author(s) -
Kaiser Reinhard P.,
Nečas David,
Cadart Timothée,
Gyepes Robert,
Císařová Ivana,
Mosinger Jiří,
Pospíšil Lubomír,
Kotora Martin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908348
Subject(s) - intramolecular force , fluorescence , electrochemistry , chemistry , catalysis , molecule , photochemistry , carbon fibers , stereochemistry , materials science , organic chemistry , physics , electrode , optics , composite number , composite material
This work presents a general approach for synthesis of substituted [5]‐helical dispiroindeno[2,1‐ c ]fluorenes based on Rh‐catalyzed intramolecular cyclotrimerization of triynes. This approach was further extended for the first synthesis of configurationally stable [7]‐helical dispiroindeno[2,1‐ c ]fluorenes. A series of variously substituted derivatives was prepared and their photophysical and electrochemical properties were evaluated. Their fluorescence emission maxima were in the region of 351–428 nm and quantum yields up to 88 % are the highest measured among the full‐carbon helical compounds.