ORGANIC
LETTERS
2010
Vol. 12, No. 19
4360-4363
DIBPillar[n]arenes (n ) 5, 6): Syntheses,
X-ray Crystal Structures, and
Complexation with n-Octyltriethyl
Ammonium Hexafluorophosphate
Chengyou Han,† Fengying Ma,† Zibin Zhang,† Binyuan Xia,† Yihua Yu,‡ and
Feihe Huang*,†
Department of Chemistry, Zhejiang UniVersity, Hangzhou 310027, P. R. China, and
Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China
Normal UniVersity, Shanghai 200062, P. R. China
Received August 5, 2010
ABSTRACT
DIBPillar[n]arenes (n ) 5, 6) were synthesized. They showed different host-guest properties with n-octyltriethyl ammonium hexafluorophosphate
G due to their different cavity sizes. DIBpillar[5]arene showed no complexation with G, while DIBpillar[6]arene formed a 1:1 complex with G
with an association constant of 334 ((24) M-1 in chloroform. In this letter, the first pillar[6]arene crystal structure and the first investigation
of the host-guest chemistry of pillar[6]arenes are reported.
The preparation of novel macrocyclic hosts is very important
since it is one of the major driving forces to accelerate the
development of supramolecular chemistry.1,2 Pillar[5]arenes,
a new kind of macrocyclic hosts, were first synthesized by
Ogoshi et al.2a by a Lewis acid catalyzed condensation
reaction of 1,4-dimethoxybenzene and paraformaldehyde in
22% yield. Then, Cao and co-workers3 improved the yields
of pillararenes to 75-95% using the condensation of 1,4-
dialkoxy-2,5-bis(alkoxymethyl)benzene catalyzed by p-tolu-
enesulfonic acid with a disadvantage of starting materials
† Zhejiang University.
‡ East China Normal University.
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10.1021/ol1018344 2010 American Chemical Society
Published on Web 09/10/2010