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Dual Association Modes of the 2,5,8‐Tris(pentafluorophenyl)phenalenyl Radical
Author(s) -
Uchida Kazuyuki,
Hirao Yasukazu,
Kurata Hiroyuki,
Kubo Takashi,
Hatano Sayaka,
Inoue Katsuya
Publication year - 2014
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.201402187
Subject(s) - stack (abstract data type) , moiety , dimer , tris , chemistry , dual mode , dual (grammatical number) , polymer chemistry , duality (order theory) , stereochemistry , organic chemistry , mathematics , pure mathematics , computer science , electronic engineering , biochemistry , engineering , programming language , art , literature
Abstract The 2,5,8‐tris(pentafluorophenyl)phenalenyl radical was obtained by a straightforward synthesis in 11 steps from 2,7‐dibromonaphthalene. This radical crystallized as a σ dimer from a solution in MeCN and as a π‐stack from a melted liquid. The π stack was not confined to dimerization, but extended into a uniform 1D stack with an interplanar distance of 3.503 Å. This unique duality in association mode arose from the thermodynamic stability of the phenalenyl moiety.