Premium
Four‐Step Domino Reaction Enables Fully Controlled Non‐Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups **
Author(s) -
Grau Benedikt W.,
Dill Maximilian,
Hampel Frank,
Kahnt Axel,
Jux Norbert,
Tsogoeva Svetlana B.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202104437
Subject(s) - domino , combinatorial chemistry , chromophore , aryl , cascade reaction , yield (engineering) , molecular electronics , chemistry , nanotechnology , oled , benzene , materials science , molecule , organic chemistry , catalysis , alkyl , layer (electronics) , metallurgy
Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular‐scale devices, organic light‐emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom‐economical and high‐yielding metal‐free four‐step domino reaction using nitrostyrenes and α,α‐dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.