Synthesis and Characterization of Annulene-Fused Pseudorotaxanes

Abstract

A 24-crown-8 ether-fused dehydrobenzo[18]annulene has been prepared via a stepwise Pd/Cu-mediated strategy. This annulene-crown ether hybrid forms a pseudorotaxane complex in CD₂Cl₂ with dibenzylammonium hexafluorophosphate when they are combined in a 1:1 ratio, as indicated by ¹H NMR spectroscopy and mass spectrometry.

Key words

annulenes - crown compounds - macrocycles - pseudorotaxanes - supramolecular chemistry

References

• 2 Haley MM. Pak JJ. Brand SC. Top. Curr. Chem.  1999,  201:  81 
• 3 Haley MM. Wan WB. In Advances in Strained and Interesting Organic Molecules   Vol. 8:  Halton B. JAI Press; New York: 2000.  p.1-41  
• Inter alia:
• 4a Baughman RH. Galvao DS. Nature   1993,  365:  635 
• 4b He CB. Liu PW. Griffin AC. Macromolecules  1998,  31:  3145 
• 4c Grima JN. Evans KE. Chem. Commun.  2000,  1531 
• For relevant acetylene-containing examples, inter alia:
• 5a Gardner GB. Venkataraman D. Moore JS. Lee S. Nature  1995,  374:  792 
• 5b Coates GW. Dunn AR. Henling LM. Dougherty DA. Grubbs RH. Angew. Chem., Int. Ed. Engl.  1997,  36:  248 
• 5c Kiang Y.-H. Gardner GB. Lee S. Xu Z. Lobkovsky EB. J. Am. Chem. Soc.  1999,  121:  8204 
• 5d Kolotuchin SV. Thiessen PA. Fenlon EE. Wilson SR. Loweth CJ. Zimmerman SC. Chem.-Eur. J.  1999,  5:  2537 
• 5e Kiang Y.-H. Gardner GB. Lee S. Xu Z. J. Am. Chem. Soc.  2000,  122:  6871 
• 5f Xu Z. Lee S. Kiang Y.-H. Mallik AB. Tsomaia N. Mueller KT. Adv. Mater.  2001,  13:  637 
• 5g

  See also Refs. [11] [12]

• 6 Baldwin KP. Matzger AJ. Scheiman DA. Tessier CA. Vollhardt KPC. Youngs WJ. Synlett  1995,  1215 
• 7 Enkelmann V. Adv. Polym. Sci.  1984,  63:  91 
• 8a Boese R. Matzger AJ. Vollhardt KPC. J. Am. Chem. Soc.  1997,  119:  2052 
• 8b Haley MM. Bell ML. English JJ. Johnson CA. Weakley TJR. J. Am. Chem. Soc.  1997,  119:  2956 
• 8c Tovar JD. Jux N. Jarrosson T. Khan SI. Rubin Y. J. Org. Chem.  1997,  62:  3432 
• 8d Correction: Tovar JD. Jux N. Jarroson T. Khan SI. Rubin Y. J. Org. Chem.  1998,  63:  4856 
• 8e Bunz UHF. Enkelmann V. Chem.-Eur. J.  1999,  5:  263 
• 8f Pak JJ. Weakley TJR. Haley MM. J. Am. Chem. Soc.  1999,  121:  8182 
• 8g Bell ML. Chiechi RC. Johnson CA. Kimball DB. Matzger AJ. Wan WB. Weakley TJR. Haley MM. Tetrahedron  2001,  57:  3507 
• 9a Fyfe MCT. Stoddart JF. Acc. Chem. Res.  1997,  30:  393 
• 9b Lehn J.-M. Supramolecular Chemistry   VCH; Weinheim: 1995. 
• 9c Comprehensive Supramolecular Chemistry   Atwood JL. Davies JED. MacNicol DD. Vögtle F. Pergamon; Oxford: 1996. 
• 9d Schneider H.-J. Yatsimirsky A. Principles and Methods in Supramolecular Chemistry   Wiley; Chichester: 2000. 
• 9e Desiraju GR. Nature  2001,  412:  397 
• Inter alia:
• 10a Lindsey JS. New J. Chem.  1991,  153 
• 10b Philp D. Stoddart JF. Synlett  1991,  445 
• 10c Whitesides GM. Mathias JP. Seto CT. Science  1991,  154:  1312 
• 10d Lawrence DS. Jiang T. Levett M. Chem. Rev.  1995,  95:  2229 
• 10e Amabilino DB. Stoddart JF. Chem. Rev.  1995,  95:  2725 
• 10f Philp D. Stoddart JF. Angew. Chem., Int. Ed. Engl.  1996,  35:  1154 
• 10g Jäger R. Vögtle F. Angew. Chem., Int. Ed. Engl.  1997,  36:  930 
• 10h Stang PJ. Olenyuk B. Acc. Chem. Res.  1997,  30:  502 
• 10i Conn MM. Rebek J. Chem. Rev.  1997,  97:  1647 
• 10j Linton B. Hamilton AD. Chem. Rev.  1997,  97:  1669 
• 10k Fujita M. Chem. Soc. Rev.  1998,  27:  417 
• 10l Breen TL. Tien J. Oliver SRJ. Hadzie T. Whitesides GM. Science  1999,  284:  948 
• 10m Breault GA. Hunter CA. Mayers PC. Tetrahedron  1999,  55:  5265 
• 10n Lindoy LF. Atkinson IM. Self-Assembly in Supramolecular Systems, In Monographs in Supramolecular Chemistry   Stoddart JF. Royal Society of Chemistry; Cambridge: 2000. 
• 10o Balzani V. Credi A. Raymo FM. Stoddart JF. Angew. Chem. Int. Ed.  2000,  39:  3348 
• 10p Zimmerman SC. Lawless LJ. Top. Curr. Chem.  2001,  217:  95 
• 11 Xiao J. Yang M. Lauher JW. Fowler FW. Angew. Chem. Int. Ed.  2000,  39:  2132 
• 12 Sarkar A. Okada S. Matsuzawa H. Matsuda H. Nakanishi H. J. Mater. Chem.  2000,  10:  819 ; and references cited therein
• Inter alia:
• 13a Ashton PR. Chrystal EJT. Glink PT. Menzer S. Schiavo C. Spencer N. Stoddart JF. Tasker PA. White AJP. Williams DJ. Chem.-Eur. J.  1996,  2:  709 
• 13b Glink PT. Schiavo C. Stoddart JF. Williams DJ. Chem. Commun.  1996,  1483 
• 13c Glink PT. Stoddart JF. Pure Appl. Chem.  1998,  70:  419 
• 13d Fyfe MCT. Stoddart JF. Adv. Supramol. Chem.  1999,  5:  1 
• 13e Cantrill SJ. Pease AR. Stoddart JF. J. Chem. Soc., Dalton Trans.  2000,  3715 
• 13f Kolchinski AG. Busch DH. Alcock NW. J. Chem. Soc., Chem. Commun.  1995,  1289 
• 13g Hubin TJ. Kolchinski AG. Vance AL. Busch DH. Adv. Supramol. Chem.  1995,  5:  237 
• 13h Yamaguchi N. Gibson HW. Angew. Chem. Int. Ed.  1999,  38:  143 
• 13i Takata T. Kihara N. Rev. Heteroatom Chem.  2000,  22:  197 
• 14 Cantrill SJ. Youn GJ. Stoddart JF. Williams DJ. J. Org. Chem.  2001,  66:  6857 
• 15 Kinder JD. Youngs WJ. Organometallics  1996,  15:  460 

1

Current address: Department of Chemistry, Idaho State University, Pocatello, ID 83209, USA.

16

Crystal data for 2: C₄₈H₃₈O₈·C₄H₈O, M _r = 814.93, yellow block, 0.22 × 0.31 × 0.41 mm, monoclinic, space group I2/a, a = 31.788(4), b = 8.6951(13), c = 35.273(4) Å, β = 113.07(1)°, V = 8970(2) ų, Z = 8, ρ_calc = 1.207 g cm^-3, Mo_{K α} radiation (λ = 0.71073 Å), µ = 0.82 cm^-1, F(000) = 3440, T = 23 °C, 2θ_max = 23.5°, 13240 independent reflections scanned, 6623 independent reflections in refinement, 550 parameters, R(F) = 0.050 [I σ(I)], wR(F ² ) = 0.068 (all data). Data were obtained on an Enraf-Nonius CAD-4 Turbo diffractometer. Structure refinement (C, O atoms anisotropic, H atoms riding) was accomplished with teXsan (v. 1.7 for SGI workstations). Crystallographic data (excluding structure factors) for 2 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-182774.