Synthesis and Characterization of Annulene-Fused Pseudorotaxanes

Joshua J.  Pak; Timothy J. R.  Weakley; Michael M.  Haley; Danny Y. K.  Lau; J. Fraser  Stoddart

doi:10.1055/s-2002-32536

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2002(9): 1256-1260
DOI: 10.1055/s-2002-32536

PAPER

Synthesis and Characterization of Annulene-Fused Pseudorotaxanes

Joshua J. Pak^a,, Timothy J. R. Weakley^a, Michael M. Haley*^a, Danny Y. K. Lau^b, J. Fraser Stoddart^b
^a Department of Chemistry, University of Oregon, Eugene, OR 97403-1253 USA
Fax: +1(541)3460487; e-Mail: haley@oregon.uoregon.edu;
^b Department of Chemistry, University of California - Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095 USA
Fax: +1(310)2061843; e-Mail: stoddart@chem.ucla.edu;

Weitere Informationen

Publikationsverlauf

Received 1 April 2002
Publikationsdatum:
28. Juni 2002 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

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

Google Scholar
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

Google Scholar
Inter alia:
4a Baughman RH. Galvao DS. Nature 1993, 365: 635

Crossref Google Scholar
4b He CB. Liu PW. Griffin AC. Macromolecules 1998, 31: 3145

Crossref Google Scholar
4c Grima JN. Evans KE. Chem. Commun. 2000, 1531

Crossref Google Scholar
For relevant acetylene-containing examples, inter alia:
5a Gardner GB. Venkataraman D. Moore JS. Lee S. Nature 1995, 374: 792

Crossref Google Scholar
5b Coates GW. Dunn AR. Henling LM. Dougherty DA. Grubbs RH. Angew. Chem., Int. Ed. Engl. 1997, 36: 248

Crossref Google Scholar
5c Kiang Y.-H. Gardner GB. Lee S. Xu Z. Lobkovsky EB. J. Am. Chem. Soc. 1999, 121: 8204

Crossref Google Scholar
5d Kolotuchin SV. Thiessen PA. Fenlon EE. Wilson SR. Loweth CJ. Zimmerman SC. Chem.-Eur. J. 1999, 5: 2537

Crossref Google Scholar
5e Kiang Y.-H. Gardner GB. Lee S. Xu Z. J. Am. Chem. Soc. 2000, 122: 6871

Crossref Google Scholar
5f Xu Z. Lee S. Kiang Y.-H. Mallik AB. Tsomaia N. Mueller KT. Adv. Mater. 2001, 13: 637

Crossref Google Scholar
5g
See also Refs. [11] [12]

Crossref Google Scholar
6 Baldwin KP. Matzger AJ. Scheiman DA. Tessier CA. Vollhardt KPC. Youngs WJ. Synlett 1995, 1215

Artikel in Thieme Connect Google Scholar
7 Enkelmann V. Adv. Polym. Sci. 1984, 63: 91

Google Scholar
8a Boese R. Matzger AJ. Vollhardt KPC. J. Am. Chem. Soc. 1997, 119: 2052

Crossref Google Scholar
8b Haley MM. Bell ML. English JJ. Johnson CA. Weakley TJR. J. Am. Chem. Soc. 1997, 119: 2956

Crossref Google Scholar
8c Tovar JD. Jux N. Jarrosson T. Khan SI. Rubin Y. J. Org. Chem. 1997, 62: 3432

Crossref Google Scholar
8d Correction: Tovar JD. Jux N. Jarroson T. Khan SI. Rubin Y. J. Org. Chem. 1998, 63: 4856

Crossref Google Scholar
8e Bunz UHF. Enkelmann V. Chem.-Eur. J. 1999, 5: 263

Crossref Google Scholar
8f Pak JJ. Weakley TJR. Haley MM. J. Am. Chem. Soc. 1999, 121: 8182

Crossref Google Scholar
8g Bell ML. Chiechi RC. Johnson CA. Kimball DB. Matzger AJ. Wan WB. Weakley TJR. Haley MM. Tetrahedron 2001, 57: 3507

Crossref Google Scholar
9a Fyfe MCT. Stoddart JF. Acc. Chem. Res. 1997, 30: 393

Crossref Google Scholar
9b Lehn J.-M. Supramolecular Chemistry VCH; Weinheim: 1995.

Crossref Google Scholar
9c Comprehensive Supramolecular Chemistry Atwood JL. Davies JED. MacNicol DD. Vögtle F. Pergamon; Oxford: 1996.

Crossref Google Scholar
9d Schneider H.-J. Yatsimirsky A. Principles and Methods in Supramolecular Chemistry Wiley; Chichester: 2000.

Crossref Google Scholar
9e Desiraju GR. Nature 2001, 412: 397

Crossref Google Scholar
Inter alia:
10a Lindsey JS. New J. Chem. 1991, 153

Google Scholar
10b Philp D. Stoddart JF. Synlett 1991, 445

Google Scholar
10c Whitesides GM. Mathias JP. Seto CT. Science 1991, 154: 1312

Google Scholar
10d Lawrence DS. Jiang T. Levett M. Chem. Rev. 1995, 95: 2229

Google Scholar
10e Amabilino DB. Stoddart JF. Chem. Rev. 1995, 95: 2725

Google Scholar
10f Philp D. Stoddart JF. Angew. Chem., Int. Ed. Engl. 1996, 35: 1154

Google Scholar
10g Jäger R. Vögtle F. Angew. Chem., Int. Ed. Engl. 1997, 36: 930

Google Scholar
10h Stang PJ. Olenyuk B. Acc. Chem. Res. 1997, 30: 502

Google Scholar
10i Conn MM. Rebek J. Chem. Rev. 1997, 97: 1647

Google Scholar
10j Linton B. Hamilton AD. Chem. Rev. 1997, 97: 1669

Google Scholar
10k Fujita M. Chem. Soc. Rev. 1998, 27: 417

Google Scholar
10l Breen TL. Tien J. Oliver SRJ. Hadzie T. Whitesides GM. Science 1999, 284: 948

Google Scholar
10m Breault GA. Hunter CA. Mayers PC. Tetrahedron 1999, 55: 5265

Google Scholar
10n Lindoy LF. Atkinson IM. Self-Assembly in Supramolecular Systems, In Monographs in Supramolecular Chemistry Stoddart JF. Royal Society of Chemistry; Cambridge: 2000.

Google Scholar
10o Balzani V. Credi A. Raymo FM. Stoddart JF. Angew. Chem. Int. Ed. 2000, 39: 3348

Google Scholar
10p Zimmerman SC. Lawless LJ. Top. Curr. Chem. 2001, 217: 95

Google Scholar
11 Xiao J. Yang M. Lauher JW. Fowler FW. Angew. Chem. Int. Ed. 2000, 39: 2132

Crossref Google Scholar
12 Sarkar A. Okada S. Matsuzawa H. Matsuda H. Nakanishi H. J. Mater. Chem. 2000, 10: 819 ; and references cited therein

Crossref Google Scholar
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

Google Scholar
13b Glink PT. Schiavo C. Stoddart JF. Williams DJ. Chem. Commun. 1996, 1483

Google Scholar
13c Glink PT. Stoddart JF. Pure Appl. Chem. 1998, 70: 419

Google Scholar
13d Fyfe MCT. Stoddart JF. Adv. Supramol. Chem. 1999, 5: 1

Google Scholar
13e Cantrill SJ. Pease AR. Stoddart JF. J. Chem. Soc., Dalton Trans. 2000, 3715

Google Scholar
13f Kolchinski AG. Busch DH. Alcock NW. J. Chem. Soc., Chem. Commun. 1995, 1289

Google Scholar
13g Hubin TJ. Kolchinski AG. Vance AL. Busch DH. Adv. Supramol. Chem. 1995, 5: 237

Google Scholar
13h Yamaguchi N. Gibson HW. Angew. Chem. Int. Ed. 1999, 38: 143

Google Scholar
13i Takata T. Kihara N. Rev. Heteroatom Chem. 2000, 22: 197

Google Scholar
14 Cantrill SJ. Youn GJ. Stoddart JF. Williams DJ. J. Org. Chem. 2001, 66: 6857

Crossref Google Scholar
15 Kinder JD. Youngs WJ. Organometallics 1996, 15: 460

Crossref Google Scholar

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) Å³, 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.