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Multi‐input–Multi‐output Molecular Response System Based on Dynamic Redox Behavior of Hexaphenylethane‐type Electron Donors with the Tetrahydrophenanthrazepine Skeleton: Strong Chiroptical Signals through the Transmission of Point Chirality to Helicity
Author(s) -
Suzuki Takanori,
Tanaka Shoko,
Kawai Hidetoshi,
Fujiwara Kenshu
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600299
Subject(s) - redox , chemistry , protonation , chirality (physics) , electron , electron transfer , photochemistry , ring (chemistry) , helicity , azepine , cationic polymerization , chemical physics , stereochemistry , crystallography , physics , polymer chemistry , inorganic chemistry , quantum mechanics , organic chemistry , ion , chiral symmetry breaking , nambu–jona lasinio model , quark
The title heterocyclic donors undergo reversible CC bond formation/cleavage upon electron transfer (dynamic redox behavior). The helical sense in both neutral and cationic states is interconvertible by facile ring flipping. The π‐type asymmetric center on the azepine nitrogen atom induces a significant degree of diasteromeric preference, thus endowing strong CD activity based on exciton coupling. Chiroptical properties could be modified not only by redox reactions but also by heat and protonation. The present redox pairs can serve as unprecedented three‐way‐input (e, H + , Δ) and two‐way‐output (UV/Vis, CD) response systems.