Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 695, Issue 1, Pages 111-119Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2009.09.035
Keywords
Molecular clip; Porphyrin; Rigid spacer; Self-assembly
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Funding
- Korea Science and Engineering Foundation (KOSEF) through BK21 (2006) program
- World Class University (WCU) program [R31-2008-000-10035-0]
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We have synthesized molecular-clip-based cofacial zinc-porphyrin complexes. The complexes are shown to be new efficient receptors for the complexation of 1,4-diazabicyclo[2,2,2] octane, acridinium ions, 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA) and 1,2,4,5-benzenetetracarboxylic dianhydride (BTDA). Large binding constants (K-asso) in the range of 2.0 x 10(4)-1.1 x 10(8) M (1) were obtained for the 1:1 complexes of molecular tweezers (3) and rectangle (8) by inserting the hosts between the two porphyrin rings. The values of K and the spectroscopic results suggest that 3 and 8 serve as effective building blocks to capture the hosts. Semi-empirical calculations show that the guests position themselves within the cleft of the bis-porphyrins. (C) 2009 Elsevier B. V. All rights reserved.
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