title: Alkynylated diazadioxaacenes: syntheses and properties.
abstract: We report the successful synthesis of a series of ethynylated dioxadiazaacenes and investigate their properties. We developed a modular Cu-based catalytic procedure to build up [1,4]dioxino[2,3-b]pyrazine motifs starting from only a few building blocks. TIPS-acetylene-substituted benzene-1,2-diol and naphthalene-2,3-diol were reacted with 2,3-dichloropyrazine, 2,3-dichloroquinoxaline, and 2,3-dichlorobenzoquinoxaline to give a set of six novel and well-soluble dioxadiazaacenes. Different reaction conditions for the coupling were tested. Copper catalysis is most effective and gave the best yield of dioxadiazaacenes. The resulting azaoxaacenes were characterized in terms of optical and electronic properties and crystal packing.
authors: Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg.
authors: Manuel
authors: M
authors: Schaffroth
authors: Benjamin D
authors: BD
authors: Lindner
authors: Vladislav
authors: V
authors: Vasilenko
authors: Frank
authors: F
authors: Rominger
authors: U H F
authors: UH
authors: Bunz
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000737:chemistry*; D011789:Quantum Theory
chemical_list: D001372:Aza Compounds; D011719:Pyrazines; D003300:Copper