Conformational control of hydrogen-bonded aromatic bis-ureas

Langmuir

Volumn 28, Issue 19, 2012, Pages 7535-7541

  Isare, Benjamin ^a   Pembouong, Gaëlle ^a   Boué, François ^b   Bouteiller, Laurent ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b DIF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL CONTROL; CONFORMATIONAL PREORGANIZATION; HIGH TEMPERATURE; INTERMOLECULAR INTERACTIONS; LOW CONCENTRATIONS; METHYL GROUP; NON-COPLANAR CONFORMATIONS; ORTHO POSITION; PHENYL MOIETIES; PHENYLUREAS; SELF-ASSEMBLED; SELF-ASSOCIATIONS; STERIC HINDRANCES; SUPRAMOLECULAR ARCHITECTURES; SYNTHONS;

AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; FUNCTIONAL GROUPS; HYDROGEN; HYDROGEN BONDS; NANOTUBES; SUPRAMOLECULAR CHEMISTRY; TOLUENE; UREA;

METABOLISM;

EID: 84861125087     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la300887p     Document Type: Article

References (60)

1. Brooks, S. J.; Edwards, P. R.; Gale, P. A.; Light, M. E. Carboxylate Complexation by a Family of Easy-to-Make Orthophenylenediamine Based Bis-Ureas: Studies in Solution and the Solid State New J. Chem. 2006, 30, 65-70
2. Pinault, T.; Cannizzo, C.; Andrioletti, B.; Ducouret, G.; Lequeux, F.; Bouteiller, L. Anions as Efficient Chain Stoppers for Hydrogen Bonded Supramolecular Polymers Langmuir 2009, 25, 8404-8407
3. Raatikainen, K.; Beyeh, N. K.; Rissanen, K. Tri- and Tetraurea Piperazine Cyclophanes: Synthesis and Complexation Studies of Preorganized and Folded Receptor Molecules Chem.-Eur. J. 2010, 16, 14554-14564
4. Mousseau, J. J.; Xing, L.; Tang, N.; Cuccia, L. A. Design and Synthesis of Urea-Linked Aromatic Oligomers-A Route Towards Convoluted Foldamers Chem.-Eur. J. 2009, 15, 10030-10038
5. Etter, M. C.; Urbanczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panunto, T. W. Hydrogen Bond Directed Cocrystallization and Molecular Recognition Properties of Diarylureas J. Am. Chem. Soc. 1990, 112, 8415-8426
6. Laliberté, D.; Maris, T.; Wuest, J. D. Molecular tectonics. Use of Urethanes and Ureas Derived from Tetraphenylmethane and Tetraphenylsilane to Build Porous Chiral Hydrogenbonded Networks Can. J. Chem. 2004, 82, 386-398
7. Custelcean, R. Crystal Engineering with Urea and Thiourea Hydrogen-Bonding Groups Chem. Commun. 2008, 295-307
8. Yang, J.; Dewal, M. B.; Sobransingh, D.; Smith, M. D.; Xu, Y.; Shimizu, L. S. Examination of the Structural Features That Favor the Columnar Self-Assembly of Bis-urea Macrocycles J. Org. Chem. 2009, 74, 102-110
9. van Esch, J.; Schoonbeek, F.; de Loos, M.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Cyclic Bis-Urea Compounds as Gelators for Organic Solvents Chem.-Eur. J. 1999, 5, 937-950
10. van der Laan, S.; Feringa, B. L.; Kellogg, R. M.; van Esch, J. Remarkable Polymorphism in Gels of New Azobenzene Bis-urea Gelators Langmuir 2002, 18, 7136-7140
11. Mohmeyer, N.; Schmidt, H.-W. A New Class of Low-Molecular-Weight Amphiphilic Gelators Chem.-Eur. J. 2005, 11, 863-872
12. Mohmeyer, N.; Schmidt, H.-W. Synthesis and Structure-Property Relationships of Amphiphilic Organogelators Chem.-Eur. J. 2007, 13, 4499-4509
13. Kishikawa, K.; Nakahara, S.; Nishikawa, Y.; Kohmoto, S.; Yamamoto, M. A Ferroelectrically Switchable Columnar Liquid Crystal Phase with Achiral Molecules: Superstructures and Properties of Liquid Crystalline Ureas J. Am. Chem. Soc. 2005, 127, 2565-2571
14. Boileau, S.; Bouteiller, L.; Lauprêtre, F.; Lortie, F. Soluble Supramolecular Polymers Based on Urea Compounds New J. Chem. 2000, 24, 845-848
15. van Gorp, J. J.; Vekemans, J. A. J. M.; Meijer, E. W. C3-Symmetrical Supramolecular Architectures: Fibers and Organic Gels from Discotic Trisamides and Trisureas J. Am. Chem. Soc. 2002, 124, 14759-14769
16. Simic, V.; Bouteiller, L.; Jalabert, M. Highly Cooperative Formation of Bis-Urea Based Supramolecular Polymers J. Am. Chem. Soc. 2003, 125, 13148-13154
17. Colombani, O.; Bouteiller, L. Selective Synthesis of Non-Symmetrical Bis-Ureas and Their Self-Assembly New J. Chem. 2004, 28, 1373-1382
18. Lortie, F.; Boileau, S.; Bouteiller, L.; Chassenieux, C.; Lauprêtre, F. Chain Stopper Assisted Characterization of Supramolecular Polymers Macromolecules 2005, 38, 5283-5287
19. Cazacu, A.; Tong, C.; van der Lee, A.; Fyles, T. M.; Barboiu, M. Columnar Self-Assembled Ureido Crown Ethers: An Example of Ion-Channel Organization in Lipid Bilayers J. Am. Chem. Soc. 2006, 128, 9541-9548
20. Bouteiller, L. Assembly via Hydrogen Bonds of Low Molar Mass Compounds into Supramolecular Polymers Adv. Polym. Sci. 2007, 207, 79-112
21. Obert, E.; Bellot, M.; Bouteiller, L.; Andrioletti, F.; Lehen-Ferrenbach, C.; Boué, F. Both Water and Organo-Soluble Supramolecular Polymer Stabilized by Hydrogen Bonding and Hydrophobic Interactions J. Am. Chem. Soc. 2007, 129, 15601-15605
22. Sabadini, E.; Francisco, K. R.; Bouteiller, L. Bis-Urea Based Supramolecular Polymer: The First Self-Assembled Drag Reducer for Hydrocarbon Solvents Langmuir 2010, 26, 1482-1486
23. Nieuwenhuizen, M. M. L.; de Greef, T. F. A.; van der Bruggen, R. L. J.; Paulusse, J. M. J.; Appel, W. P. J.; Smulders, M. M. J.; Sijbesma, R. P.; Meijer, E. W. Self-Assembly of Ureido-Pyrimidinone Dimers into One-Dimensional Stacks by Lateral Hydrogen Bonding Chem.-Eur. J. 2010, 16, 1601-1612
24. Colombani, O.; Barioz, C.; Bouteiller, L.; Chanéac, C.; Fompérie, L.; Lortie, F.; Montès, H. Attempt Toward 1D Cross-Linked Thermoplastic Elastomers: Structure and Mechanical Properties of a New System Macromolecules 2005, 38, 1752-1759
25. Das, S.; Yilgor, I.; Yilgor, E.; Inci, B.; Tezgel, O.; Beyer, F. L.; Wilkes, G. L. Structure-Property Relationships and Melt Rheology of Segmented, Non-Chain Extended Polyureas: Effect of Soft Segment Molecular Weight Polymer 2007, 48, 290-301
26. Das, S.; Yilgor, I.; Yilgor, E.; Wilkes, G. L. Probing the Urea Hard Domain Connectivity in Segmented, Non-Chain Extended Polyureas Using Hydrogen-Bond Screening Agents Polymer 2008, 49, 174-179
27. Ouhib, F.; Bugnet, E.; Nossov, A.; Bonardet, J.-L.; Bouteiller, L. Microporous Polyacrylate Matrix Containing Hydrogen Bonded Nanotubular Assemblies Polymer 2010, 51, 3360-3364
28. Courtois, J.; Baroudi, I.; Nouvel, N.; Degrandi, E.; Pensec, S.; Ducouret, G.; Chanéac, C.; Bouteiller, L.; Creton, C. Supramolecular Soft Adhesive Materials Adv. Funct. Mater. 2010, 20, 1803-1811
29. Pensec, S.; Nouvel, N.; Guilleman, A.; Creton, C.; Boué, F.; Bouteiller, L. Self-Assembly in Solution of a Reversible Comb-Shaped Supramolecular Polymer Macromolecules 2010, 43, 2529-2534
30. Vonau, F.; Suhr, D.; Aubel, D.; Bouteiller, L.; Reiter, G.; Simon, L. Evolution of Multilevel Order in Supramolecular Assemblies Phys. Rev. Lett. 2005, 94, 066103
31. Vonau, F.; Aubel, D.; Bouteiller, L.; Reiter, G.; Simon, L. Cooperative Rearrangements Leading to Long Range Order in Monolayers of Supramolecular Polymers Phys. Rev. Lett. 2007, 99, 086103
32. Vonau, F.; Linares, M.; Isare, B.; Aubel, D.; Habar, M.; Bouteiller, L.; Reiter, G.; Geskin, V.; Zerbetto, F.; Lazzaroni, R.; Simon, L. Branched Substituents Generate Improved Supramolecular Ordering in Physisorbed Molecular Assemblies J. Phys. Chem. C 2009, 113, 4955-4959
33. Cho, Y. L.; Rudkevich, D. M.; Shivanyuk, A.; Rissanen, K.; Rebek, J., Jr. Hydrogen-Bonding Effects in Calix[4]arene Capsules Chem.-Eur. J. 2000, 6, 3788-3796
34. Alajarin, M.; Pastor, A.; Orenes, R.-A.; Steed, J. W.; Arakawa, R. Self-Assembly of Tris(2-ureidobenzyl)amines: A New Type of Capped, Capsule-Like DimericAggregates Derived from a Highly Flexible Skeleton Chem.-Eur. J. 2004, 10, 1383-1397
35. Shivanyuk, A.; Saadioui, M.; Broda, F.; Thondorf, I.; Vysotsky, M. O.; Rissanen, K.; Kolehmainen, E.; Böhmer, V. Sterically and Guest-Controlled Self-Assembly of Calix[4]arene Derivatives Chem.-Eur. J. 2004, 10, 2138-2148
36. Rudzevich, Y.; Rudzevich, V.; Böhmer, V. Fine-Tuning the Dimerization of Tetraureacalix[4]arenes Chem.-Eur. J. 2010, 16, 4541-4549
37. Emery, R.; Macleod, N. A.; Snoek, L. C.; Simons, J. P. Conformational Preferences in Model Antiviral Compounds: A Spectroscopic and Computational Study of Phenylurea and 1,3-Diphenylurea Phys. Chem. Chem. Phys. 2004, 6, 2816-2820
38. Bryantsev, V. S.; Firman, T. K.; Hay, B. P. Conformational Analysis and Rotational Barriers of Alkyl- and Phenyl-Substituted Urea Derivatives J. Phys. Chem. A 2005, 109, 832-842
39. 2O Cryst. Struct. Commun. 1979, 8, 429-432
40. Ciajolo, M. R.; Leli, F.; Tancredi, T.; Temussi, P. A.; Tuzi, A. Structure Analysis of two Conformationally Flexible Sapidants, o-and p -Tolylurea Acta Crystallogr. 1982, B38, 2928-2930
41. George, S.; Nangia, A. N, N ′-Bis(4-biphenylyl)urea Acta Crystallogr. 2003, E59, 901-902
42. Koevoets, R. A.; Versteegen, R. M.; Kooijman, H.; Spek, A. L.; Sijbesma, R. P.; Meijer, E. W. Molecular Recognition in a Thermoplastic Elastomer J. Am. Chem. Soc. 2005, 127, 2999-3003
43. Bowles, P.; Clayden, J.; Helliwell, M.; McCarthy, C.; Tomkinson, M.; Westlund, N. Atroposelectivity in the Reactions of Ortholithiated Aromatic Tertiary Amides With Aldehydes J. Chem. Soc., Perkin Trans.1 1997, 2607-2616
44. Bushey, M. L.; Hwang, A.; Stephens, P. W.; Nuckolls, C. Enforced Stacking in Crowded Arenes J. Am. Chem. Soc. 2001, 123, 8157-8158
45. Gonzales-Gonzales, J. S.; Martinez-Martinez, F. J.; Campos, A. L. P.; Rosales-Hoz, M. J.; Garcia-Baez, E. V.; Padilla-Martinez, I. I. Supramolecular Architectures of Conformationally Controlled 1,3-Phenyldioxalamic Molecular Clefts Through Hydrogen Bonding and Steric Restraints CrystEngComm 2011, 13, 4748-4761
46. Helzy, F.; Maris, T.; Wuest, J. D. Engineering Hydrogen-Bonded Molecular Crystals Built from 1,3,5-Substituted Derivatives of Benzene: 6,6′,6″-(1,3,5-Phenylene)tris-1,3,5-triazine-2,4-diamines Cryst. Growth Des. 2008, 8, 1547-1553
47. Bouteiller, L.; Colombani, O.; Lortie, F.; Terech, P. Thickness Transition of a Rigid Supramolecular Polymer J. Am. Chem. Soc. 2005, 127, 8893-8898
48. Roman, M.; Cannizzo, C.; Pinault, T.; Isare, B.; Andrioletti, B.; van der Schoot, P.; Bouteiller, L. Supramolecular Balance: Using Cooperativity to Amplify Weak Interactions J. Am. Chem. Soc. 2010, 132, 16818-16824
49. Bouteiller, L.; van der Schoot, P. Probing Intermolecular Interactions in Self-Assembled Nanotubes J. Am. Chem. Soc. 2012, 134, 1363-1366
50. Pinault, T.; Isare, B.; Bouteiller, L. Solvents with Similar Bulk Properties Induce Distinct Supramolecular Architectures Chem. Phys. Chem. 2006, 7, 816-819
51. Shikata, T.; Nishida, T.; Isare, B.; Linares, M.; Lazzaroni, R.; Bouteiller, L. Structure and Dynamics of a Bisurea Based Supramolecular Polymer in n-Dodecane J. Phys. Chem. B 2008, 112, 8459-8465
52. van der Gucht, J.; Besseling, N. A. M.; Knoben, W.; Bouteiller, L.; Cohen Stuart, M. A. Brownian Particles in Supramolecular Polymer Solutions Phys. Rev. E 2003, 67, 051106
53. Knoben, W.; Besseling, N. A. M.; Bouteiller, L.; Cohen Stuart, M. A. Dynamics of Reversible Supramolecular Polymers: Independent Determination of the Dependence of Linear Viscoelasticity on Concentration and Chain Length by Using Chain Stoppers Phys. Chem. Chem. Phys. 2005, 7, 2390-2398
54. Ducouret, G.; Chassenieux, C.; Martins, S.; Lequeux, F.; Bouteiller, L. Rheological Characterisation of Bis-Urea Based Viscoelastic Solutions in an Apolar Solvent J. Colloid Interface Sci. 2007, 310, 624-629
55. Isare, B.; Linares, M.; Lazzaroni, R.; Bouteiller, L. Engineering the Cavity of Self-Assembled Dynamic Nanotubes J. Phys. Chem. B 2009, 113, 3360-3364
56. Lortie, F.; Boileau, S.; Bouteiller, L. N,N′-Disubstituted Ureas: Influence of Substituents on the Formation of Supramolecular Polymers Chem.-Eur. J. 2003, 9, 3008-3014
57. Lortie, F.; Boileau, S.; Bouteiller, L.; Chassenieux, C.; Demé, B.; Ducouret, G.; Jalabert, M.; Lauprêtre, F.; Terech, P. Structural and Rheological Study of a Bis-Urea Based Reversible Polymer in an Apolar Solvent Langmuir 2002, 18, 7218-7222
58. Bellot, M.; Bouteiller, L. Thermodynamic Description of Bis-Urea Self-Assembly: Competition Between Two Supramolecular Polymers Langmuir 2008, 24, 14176-14182
59. Arnaud, A.; Bouteiller, L. Isothermal Titration Calorimetry of Supramolecular Polymers Langmuir 2004, 20, 6858-6863
60. Ouhib, F.; Raynal, M.; Jouvelet, B.; Isare, B.; Bouteiller, L. Hydrogen Bonded Supramolecular Polymers in Moderately Polar Solvents Chem. Commun. 2011, 47, 10683-10685