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4,10‐Dibromoanthanthrone as a New Building Block for p‐Type, n‐Type, and Ambipolar π‐Conjugated Materials
Author(s) -
Giguère JeanBenoît,
Verolet Quentin,
Morin JeanFrançois
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202878
Subject(s) - ambipolar diffusion , lamellar structure , conjugated system , type (biology) , molecule , materials science , block (permutation group theory) , modulation (music) , crystallography , electron , optoelectronics , nanotechnology , chemistry , organic chemistry , polymer , physics , composite material , mathematics , ecology , geometry , quantum mechanics , acoustics , biology
New p‐type, n‐type, and ambipolar molecules were synthesized from commercially available 4,10‐dibromoanthanthrone dye. Substitution at the 4,10‐ and 6,12‐positions with different electron‐rich and electron‐poor units allowed the modulation of the optoelectronic properties of the molecules. A bis(dicyanovinylene)‐functionalized compound was also prepared with a reduction potential as low as −50 mV versus Ag + with a crystalline two‐dimensional lamellar packing arrangement. These characteristics are important prerequisites for air‐stable n‐type organic field‐effect transistor applications.