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Inne
Stereocontrolled synthesis of chiral heteroaromatic propellers with small optical bandgaps.
Autorzy
Rok wydania
2019
Czasopismo
Angewandte Chemie - International Edition
Numer woluminu
58
Strony
4929-4933
DOI
10.1002/anie.201900175
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
Chiral heteroaromatic propellers based on radially π‐extended hexapyrrolohexaazacoronenes were obtained in a concise synthesis from suitably functionalized donor–acceptor monopyrroles. To overcome steric hindrance, a new cyclodehydrogenation method was developed, and it uses bromine electrophiles as oxidative coupling agents instead of the commonly employed high‐potential oxidants. The new reaction offers high yields of propeller‐shaped targets, even for electron‐deficient precursors, and shows electrophile‐dependent stereoselectivity, with N‐bromosuccinimide and dibromine yielding, respectively D6‐ and C2‐symmetric products. The propeller azacoronenes are chiral and can be separated into configurationally stable enantiomers. In addition to providing steric bulk, peripheral functionalization considerably affects the electronic properties of the propellers, which exhibit reduced optical and electrochemical band gaps, and a more clearly defined electroreduction behavior.
Słowa kluczowe
chrality, chromophores, helicenes, macrocycles, structure elucidation
Adres publiczny
http://dx.doi.org/10.1002/anie.201900175
Strona internetowa wydawcy
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