Disproportionation and self-sorting in molecular encapsulation

Proceedings of the National Academy of Sciences of the United States of America

Volumn 106, Issue 26, 2009, Pages 10430-10434

  Ajami, Dariush ^a   Hou, Jun Li ^a   Dale, Trevor J ^a   Barrett, Elizabeth ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; METHANE; NANOMATERIAL; PARACYCLOPHANE DERIVATIVE; RECEPTOR; RESORCINARENE; SOLVENT; UNCLASSIFIED DRUG; (2.2)PARACYCLOPHANE; ETHANE; POLYCYCLIC HYDROCARBON; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; ENCAPSULATION; HYBRID; HYBRIDIZATION; HYDROGEN BOND; MOLECULAR BIOLOGY; MOLECULAR SIZE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; SELF SORTING SYSTEM; CHEMISTRY; ROTATION;

ETHANE; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NANOSTRUCTURES; POLYCYCLIC COMPOUNDS; POLYMERS; ROTATION;

EID: 67649795154     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0809903106     Document Type: Article

References (38)

1. Conn MM, Rebek J, Jr (1997) Self-assembling capsules. Chem Reviews 97:1647-1668.
2. Kusukawa T, Fujita M (1999) Ship-in-a-bottle© formation of stable hydrophobic dimers of cis-azobenzene and -stilbene derivatives in a self-assembled coordination nanocage. J Am Chem Soc 121:1397-1398. (Pubitemid 29104077)
3. Fiedler D, Bergman RG, Raymond KN (2004) Supramolecular catalysis of a unimolecular transformation: Aza-cope rearrangement within a self-assembled host. Angew Chem Int Ed 43:6748-6751. (Pubitemid 40019019)
4. Yoshizawa M, Kusukawa T, Fujita M, Yamaguchi K (201) Cavity-directed synthesis of otherwise labile silanol oligomers within self-assembled coordination cages. J Am Chem Soc 123:10454-10459. (Pubitemid 33015690)
5. Dong VM, Fiedler D, Carl B, Bergman RG, Raymond KN (2006) Molecular recognition and stabilization of iminium ions in water. J Am Chem Soc 128:14464-14465. (Pubitemid 44749838)
6. Shivanyuk A, Rebek J, Jr (2002) Social isomers in encapsulation complexes. J Am Chem Soc 124:12074-12075.
7. Kaanumalle LS, Gibb CLD, Gibb BC, Ramamurthy V (2005) A hydrophobic nanocapsule controls the photophysics of aromatic molecules by suppressing their favored solution pathways. J Am Chem Soc 127:3674-3675. (Pubitemid 40411389)
8. Corbellini F, Di Constanzo L, Crego-Calama M, Geremia S, Reinhoudt DR (2003) Guest encapsulation in a water-soluble molecular capsule based on ionic interactions. J Am Chem Soc 125:9946-9947. (Pubitemid 36994924)
9. Fujita M, et al. (2001) Molecular paneling via coordination. Chem Comm 509-518. (Pubitemid 32250675)
10. Fiedler D, Leung DH, Bergman RG, Raymond KN (2005) Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels. Acc Chem Res 38:349-358. (Pubitemid 40792597)
11. MacGillivray LR, Atwood JL (1997) A chiral spherical molecular assembly held together by 60 hydrogen bonds. Nature 389:469-472. (Pubitemid 27435316)
12. Avram L, Cohen Y (2002) Spontaneous formation of hexameric resorcinarene capsule in chloroform solution as detected by diffusion NMR. J Am Chem Soc 124:15148-15149. (Pubitemid 36014479)
13. Shivanyuk A, Rebek J, Jr (2003) Assembly of resorcinarene capsules in wet solvents. J Am Chem Soc 125:3432-3433.
14. Shivanyuk A, Rebek J, Jr (2001) Recognition of guests in solution by self-assembling resorcinarene subunits. Proc Natl Acad Sci USA 98:7662-7665.
15. Shivanyuk A, Rebek J, Jr (2001) Reversible encapsulation of multiple, neutral guests in hexameric resorcinarene hosts. Chem Comm 2424-2425.
16. Ajami D, Schramm MP, Volonterio A, Rebek J, Jr (2006) Assembly of hybrid synthetic capsules. Angew Chem Int Ed Engl 46:242-244.
17. Wu AX, Isaacs L (2003) Self-sorting: The exception or the rule? J Am Chem Soc 125:4831-4835. (Pubitemid 36505375)
18. Valdés C, Spitz UP, Toledo L, Kubik S, Rebek J, Jr (1995) Synthesis and self-assembly of pseudo-spherical homo-and heterodimeric capsules. J Am Chem Soc 117;12733-12745.
19. Wyler R, de Mendoza J, Rebek J, Jr (1993) A synthetic cavity assembles through self-complementary hydrogen bonds. Angew Chem Int Ed Eng 32:1699-1701.
20. Avram L, Cohen Y (2005) Diffusion measurements for molecular capsules: Pulse sequences effect on water signal decay. J Am Chem Soc 127:5714-5719. (Pubitemid 40569884)
21. Scarso A, Onagi H, Rebek J, Jr (2004) Mechanically regulated rotation of a guest in a nanoscale host. J Am Chem Soc 126:12728-12729.
22. Ajami D, Rebek J, Jr (2008) Gas behavior in self-assembled capsules. Angew Chemie Intl Ed Engl 47:6059-6061.
23. Castellano RK, Craig SL, Nuckolls C, Rebek J, Jr (2000) Detection and mechanistic studies of multi-component assembly by fluorescence resonance energy transfer. J Am Chem Soc 122:7876-7882.
24. Barrett ES, Dale TJ, Rebek J, Jr (2007) Synthesis and assembly of monofunctionalized pyrogallolarene capsules monitored by fluorescence resonance energy transfer. Chem Commun 4224-4226.
25. Barrett ES, Dale TJ, Rebek J, Jr (2007) Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer. J Am Chem Soc 129:3818-3819.
26. Ajami D, Iwasawa T, Rebek J, Jr (2006) Experimental and computational probes of the space in a self-assembled capsule. Proc Natl Acad Sci USA 103:8934-8936.
27. Timmerman P, Verboom W, van Veggel FCJM, van Duynhovan JPM, Reinhoudt DN (1994) A novel type of stereoisomerism in calix[4]arene-based carceplexes. Angew Chem Int Ed Eng 33:2345-2348. (Pubitemid 24986109)
28. Nishio M, Hirota M, Umezawa Y (1998) in The C-H/πInteraction: Evidence, Nature, and Consequences. Stereochemistry of Organic Compounds (Wiley, New York).
29. Grotzfeld RM, Branda N, Rebek J, Jr (1996) Reversible encapsulation of disc-shaped guests by a synthetic, self-assembled host. Science 271:487-489.
30. Tiedemann BDF, Raymond KN (2006) Dangling arms: A tetrahedral supramolecular host with partially encapsulated guests. Angew Chem Int Ed 45:83-86. (Pubitemid 43003991)
31. Rivera JM, Martin T, Rebek J, Jr (1998) Structural rules governing self-assembly emerge from new molecular capsules. J Am Chem Soc 120:819-820.
32. Castellano RK, Rebek J, Jr (1998) Formation of discrete, functional assemblies and informational polymers through the hydrogen bonding preferences of calixarene aryl and sulfonyl tetraureas. J Am Chem Soc 120:3657-3663.
33. Goodsell DS, Olson AJ (2000) Structural symmetry and protein function. Annu Rev Biophys Biomol Struct 29:105-153. (Pubitemid 30599590)
34. Avram L, Cohen Y (2004) Self-recognition, structure, stability, and guest affinity of pyrogallol[4]arene and resorcin[4]arene capsules in solution J Am Chem Soc 126:11556-11563. (Pubitemid 39244972)
35. Beyeh NK, Kogej M, Aahman A, Rissanen K, Schalley CA (2006) Flying capsules: Mass spectrometric detection of pyrogallarene and resorcinarene hexamers. Angew Chem Int Ed 45:5214-5218. (Pubitemid 44238143)
36. Ajami D, Rebek J, Jr (2006) Expanded capsules with reversibly added spacers. J Am Chem Soc 128:5314-5315.
37. Ajami D, Rebek J, Jr (2007) Adaptations of guest and host in expanded self-assembled capsules. Proc Natl Acad Sci USA 104:16000-16003.
38. Rowan A, Elemans JAW, Nolte RJM (1999) Molecular and supramolecular objects from glycoluril. Acc Chem Res 32:995-1006.