Porphyrin assemblies through the air/water interface: Effect of hydrogen bond, thermal annealing, and amplification of supramolecular chirality

Langmuir

Volumn 28, Issue 15, 2012, Pages 6356-6363

  Rong, Yunlong ^a,b   Chen, Penglei ^b   Wang, Dongjun ^a   Liu, Minghua ^b  

^a HEBEI NORMAL UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AIR/WATER INTERFACES; BUILDING BLOCKES; CD SIGNALS; CHIROPTICAL PROPERTIES; COOPERATIVE INTERACTIONS; EFFECT OF HYDROGEN; HYDROPHOBIC INTERACTIONS; INTERFACIAL ASSEMBLY; INTERMOLECULAR HYDROGEN BONDS; LANGMUIR BLODGETT TECHNIQUES; MOLECULAR ASSEMBLY; MOLECULAR SKELETON; NON-COVALENT INTERACTION; PORPHINE; PORPHYRIN ASSEMBLIES; SPREADING PROPERTY; SUPRAMOLECULAR CHIRALITY; SYMMETRY-BREAKING; THERMAL ANNEALING TREATMENT; THERMAL-ANNEALING;

COMPLEXATION; PORPHYRINS; THIN FILM TRANSISTORS;

HYDROGEN BONDS;

EID: 84859904758     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la3005294     Document Type: Article

References (55)

1. Smith, D. K. Lost in Translation? Chirality Effects in the Self-Assembly of Nanostructured Gel-Phase Materials Chem. Soc. Rev. 2009, 38, 684-694
2. Kumaki, J.; Sakurai, S.-I.; Yashima, E. Visualization of Synthetic Helical Polymers by High-Resolution Atomic Force Microscopy Chem. Soc. Rev. 2009, 38, 737-746
3. Amabilino, D. B.; Veciana, J. Supramolecular Chiral Functional Materials Top. Curr. Chem. 2006, 265, 253-302 (Pubitemid 44424312)
4. Ernst, K.-H. Supramolecular Surface Chirality Top. Curr. Chem. 2006, 265, 209-252 and the references therein (Pubitemid 44420764)
5. Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. The Macromolecular Route to Chiral Amplification Angew. Chem., Int. Ed. 1999, 38, 3138-3154
6. Palmans, A. R. A.; Meijer, E. W. Amplification of Chirality in Dynamic Supramolecular Aggregates Angew. Chem., Int. Ed. 2007, 46, 8948-8968 (Pubitemid 350232745)
7. Maeda, K.; Yashima, E. Dynamic Helical Structures: Detection and Amplification of Chirality Top. Curr. Chem. 2006, 265, 47-88 (Pubitemid 44420761)
8. Weissbuch, I.; Leiserowitz, L.; Lahav, M. Stochastic "Mirror Symmetry Breaking" via Self-Assembly, Reactivity and Amplification of Chirality: Relevance to Abiotic Conditions Top. Curr. Chem. 2005, 259, 123-165 and the references therein (Pubitemid 44420802)
9. Crusats, J.; El-Hachemi, Z.; Ribó, J. M. Hydrodynamic Effects on Chiral Induction Chem. Soc. Rev. 2010, 39, 569-577
10. Qiu, Y.; Chen, P.; Liu, M. Evolution of Various Porphyrin Nanostructures via an Oil/Aqueous Medium: Controlled Self-Assembly, Further Organization, and Supramolecular Chirality J. Am. Chem. Soc. 2010, 132, 9644-9652
11. Iftime, G.; Labarthet, F. L.; Natansohn, A.; Rochon, P. Control of Chirality of an Azobenzene Liquid Crystalline Polymer with Circularly Polarized Light J. Am. Chem. Soc. 2000, 122, 12646-12650 (Pubitemid 32052191)
12. Link, D. R.; Natale, G.; Shao, R.; Maclennan, J. E.; Clark, N. A.; Körblova, E.; Walba, D. M. Spontaneous Formation of Macroscopic Chiral Domains in a Fluid Smectic Phase of Achiral Molecules Science 1997, 278, 1924-1927 (Pubitemid 28013229)
13. Choi, S.-W.; Izumi, T.; Hoshino, Y.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Circular-Polarization-Induced Enantiomeric Excess in Liquid Crystals of an Achiral, Bent-Shaped Mesogen Angew. Chem., Int. Ed. 2006, 45, 1382-1385 (Pubitemid 44097614)
14. Yamaguchi, T.; Kimura, T.; Matsuda, H.; Aida, T. Macroscopic Spinning Chirality Memorized in Spin-Coated Films of Spatially Designed Dendritic Zinc Porphyrin J-Aggregates Angew. Chem., Int. Ed. 2004, 43, 6350-6355 (Pubitemid 40029469)
15. DUrso, A.; Randazzo, R.; Faro, L. L.; Purrello, R. Vortexes and Nanoscale Chirality Angew. Chem., Int. Ed. 2010, 49, 108-112
16. Zou, G.; Jiang, H.; Zhang, Q.; Kohn, H.; Manaka, T.; Iwamoto, M. Chiroptical Switch Based on Azobenzene-Substituted Polydiacetylene LB Film under Thermal and Photic Stimuli J. Mater. Chem. 2010, 20, 285-291
17. Liu, L.; Hong, D.-J.; Lee, M. Chiral Assembly from Achiral Rod-Coil Molecules Triggered by Compression at the Air-Water Interface Langmuir 2009, 25, 5061-5067
18. Yuan, J.; Liu, M. Chiral Molecular Assemblies from a Novel Achiral Amphiphilic 2-(Heptadecyl) Naphtha[2,3]imidazole through Interfacial Coordination J. Am. Chem. Soc. 2003, 125, 5051-5056 (Pubitemid 36520434)
19. Huang, X.; Li, C.; Jiang, S.; Wang, X.; Zhang, B.; Liu, M. Self-Assembled Spiral Nanoarchitecture and Supramolecular Chirality in Langmuir-Blodgett Films of an Achiral Amphiphilic Barbituric Acid J. Am. Chem. Soc. 2004, 126, 1322-1323 (Pubitemid 38200788)
20. Zhang, Y.; Chen, P.; Jiang, L.; Hu, W.; Liu, M. Controllable Fabrication of Supramolecular Nanocoils and Nanoribbons and Their Morphology-Dependent Photoswitching J. Am. Chem. Soc. 2009, 131, 2756-2757
21. Guo, P.; Zhang, L.; Liu, M. A Supramolecular Chiroptical Switch Exclusively from an Achiral Amphiphile Adv. Mater. 2006, 18, 177-180 (Pubitemid 43133386)
22. Zhang, Y.; Chen, P.; Liu, M. A General Method for Constructing Optically Active Supramolecular Assemblies from Intrinsically Achiral Water-Insoluble Free-Base Porphyrins Chem.-Eur. J. 2008, 14, 1793-1803
23. Yao, P.; Qiu, Y.; Chen, P.; Ma, Y.; He, S.; Zheng, J.-Y.; Liu, M. Interfacial Molecular Assemblies of Metalloporphyrins with Two Trans or One Axial Ligands ChemPhysChem 2010, 11, 722-729
24. Chen, P.; Ma, X.; Hu, K.; Rong, Y.; Liu, M. Left or Right? The Direction of Compression-Generated Vortex-Like Flow Selects the Macroscopic Chirality of Interfacial Molecular Assemblies Chem.-Eur. J. 2011, 17, 12108-12114
25. Chen, P.; Ma, X.; Duan, P.; Liu, M. Chirality Amplification of Porphyrin Assemblies Exclusively Constructed from Achiral Porphyrin Derivatives ChemPhysChem 2006, 7, 2419-2423
26. Qiu, Y.; Chen, P.; Liu, M. Interfacial Assemblies of Atypical Amphiphilic Porphyrins: Hydrophobicity/Hydrophilicity of Substituents, Annealing Effects, and Supramolecular Chirality Langmuir 2010, 26, 15272-15277
27. Crego-Calama, M.; Reinhoudt, D. N.; Cate, M. G. J. T. Templation in Noncovalent Synthesis of Hydrogen-Bonded Rosettes Top. Curr. Chem. 2005, 249, 285-316 (Pubitemid 44420863)
28. Grabowski, S. J. What Is the Covalency of Hydrogen Bonding? Chem. Rev. 2011, 111, 2597-2625
29. González-Rodríguez, D.; Schenning, A. P. H. J. Hydrogen-bonded Supramolecular π-Functional Materials Chem. Mater. 2011, 23, 310-325
30. Such, G. K.; Johnston, A. P. R; Caruso, F. Engineered Hydrogen-Bonded Polymer Multilayers: From Assembly to Biomedical Applications Chem. Soc. Rev. 2011, 40, 19-29 and the references therein
31. Natale, C. D.; Monti, D.; Paolesse, R. Chemical Sensitivity of Porphyrin Assemblies Mater. Today 2010, 13, 46-52
32. Hambright, P. In The Porphyrin Handbook, Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2000; Chapter 18, pp 129-210.
33. Alessio, E. Non-Covalent Multi-Porphyrin Assemblies: Synthesis and Properties, 1 st ed.; Springer: Berlin, 2006, and the references therein.
34. 2 Gas Langmuir 2002, 18, 7594-7601 (Pubitemid 35390105)
35. Chou, H.; Chen, C.-T.; Stork, K. F.; Bohn, P. W.; Suslick, K. S. Langmuir-Blodgett Films of Amphiphilic Push-Pull Porphyrins J. Phys. Chem. 1994, 98, 383-385
36. Pasternack, R. F.; Huber, P. R.; Boyd, P.; Engasser, G.; Francesconi, L.; Gibbs, E.; Fasella, P.; Vernturo, G. C.; Hinds, L.; de, C. On the Aggregation of Meso-Substituted Water-Soluble Porphyrins J. Am. Chem. Soc. 1972, 94, 4511-4517
37. Okada, S.; Segawa, H. Substituent-Control Exciton in J-Aggregates of Protonated Water-Insoluble Porphyrins J. Am. Chem. Soc. 2003, 125, 2792-2796 (Pubitemid 36512264)
38. van Hameren, R.; Schön, P.; van Buul, A. M.; Hoogboom, J.; Lazarenko, S. V.; Gerritsen, J. W.; Engelkamp, H.; Christianen, P. C. M.; Heus, H. A.; Maan, J. C.; Rasing, T.; Speller, S.; Rowan, A. E.; Elemans, J. A. A.W.; Nolte, R. J. M. Macroscopic Hierarchical Surface Patterning of Porphyrin Trimers via Self-Assembly and Dewetting Science 2006, 314, 1433-1436 (Pubitemid 44871945)
39. Shirakawa, M.; Fujita, N.; Shinkai, S. A Stable Single Piece of Unimolecularly π-Stacked Porphyrin Aggregate in a Thixotropic Low Molecular Weight Gel: A One-Dimensional Molecular Template for Polydiacetylene Wiring up to Several Tens of Micrometers in Length J. Am. Chem. Soc. 2005, 127, 4164-4165 (Pubitemid 40463029)
40. Yao, P.; Wang, H.; Chen, P.; Zhan, X.; Kuang, X.; Zhu, D.; Liu, M. Hierarchical Assembly of an Achiral π-Conjugated Molecule into a Chiral Nanotube through the Air/Water Interface Langmuir 2009, 25, 6633-6636
41. Bull, R. A.; Bulkowski, J. E. Tetraphenylporphyrin Monolayers: Formation at the Air-Water Interface and Characterization on Glass Supports by Absorption and Fluorescence Spectroscopy J. Colloid Interface Sci. 1983, 92, 1-12
42. Scheidt, W. R. Trends in Metalloporphyrin Stereochemistry Acc. Chem. Res. 1977, 10, 339-345
43. Qian, D.-J.; Nakamura, C.; Miyake, J. Multiporphyrin Array from Interfacial Metal-Mediated Assembly and Its Langmuir-Blodgett Films Langmuir 2000, 16, 9615-9619 (Pubitemid 32032947)
44. Chen, P.; Chen, Z.; Liu, M. Nanotapes Formed through the Air/Water Interfacial Self-Assembly of a Bola-Form Pentanediamide Derivative Colloids Surf., A 2008, 313-314, 666-669
45. Guo, P.; Chen, P.; Liu, M. Shuttle-Like Supramolecular Nanostructures Formed by Self-Assembly of a Porphyrin via an Oil/Water System Nanoscale Res. Lett. 2011, 6, 529 (10 pp)
46. Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. The Exciton Model in Molecular Spectroscopy Pure Appl. Chem. 1965, 11, 371-392
47. McRae, E. G.; Kasha, M. Enhancement of Phosphorescence Ability upon Aggregation of Dye Molecules J. Chem. Phys. 1958, 28, 721-722
48. van Esch, J. H.; Feiters, M. C.; Peters, A. M.; Nolte, R. J. M. UV-Vis, Fluorescence, and EPR Studies of Porphyrins in Bilayers of Dioctadecyldimethylammonium Surfactants J. Phys. Chem. 1994, 98, 5541-5551
49. Kano, H.; Kobayashi, T. Time-Resolved Fluorescence and Absorption Spectroscopies of Porphyrin J-Aggregates J. Chem. Phys. 2002, 116, 184-195 (Pubitemid 34061813)
50. Thomas, D. W.; Martell, A. E. Metal Chelates of Tetraphenylporphine and of Some p -Substituted Derivatives J. Am. Chem. Soc. 1959, 81, 5111-5119
51. Kimura, F.; Umemura, J.; Takenaka, T. FTIR-ATR Studies on Langmuir-Blodgett Films of Stearic Acid with 1-9 Monolayers Langmuir 1986, 2, 96-101
52. Lio, A.; Reichert, A.; Ahn, D. J.; Nagy, J. O.; Salmeron, M.; Charych, D. H. Molecular Imaging of Thermochromic Carbohydrate-Modified Polydiacetylene Thin Films Langmuir 1997, 13, 6524-6532 (Pubitemid 127592070)
53. Huang, X.; Jiang, S.; Liu, M. Metal Ion Modulated Organization and Function of the Langmuir-Blodgett Films of Amphiphilic Diacetylene: Photopolymerization, Thermochromism, and Supramolecular Chirality J. Phys. Chem. B 2005, 109, 114-119 (Pubitemid 40120953)
54. Ohe, C.; Ando, H.; Sato, N.; Urai, Y.; Yamamoto, M.; Itoh, K. Carboxylate-Counterion Interactions and Changes in These Interactions during Photopolymerization of a Long-Chain Diacetylene Monocarboxylic Acid at Air-Water Interfaces: External Infrared Reflection Absorption Spectroscopic Study J. Phys. Chem. B 1999, 103, 435-444 (Pubitemid 129680706)
55. Sasaki, D. Y.; Carpick, R. W.; Burns, A. R. High Molecular Orientation in Mono- and Trilayer Polydiacetylene Films Imaged by Atomic Force Microscopy J. Colloid Interface Sci. 2000, 229, 490-496