Gelation and fluorescent organogels of a complex of perylenetetracarboxylic tetraacid with cationic surfactants

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 375, Issue 1-3, 2011, Pages 156-162

  Ren, Xiangyu ^a   Yu, Wei ^b   Zhang, Zijian ^b   Xia, Nan ^b   Fu, Guihua ^b   Lu, Xiuping ^a   Wang, Wei ^b  

^a TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Fluorescence; Organogels; Perylene; stacking

Indexed keywords

AGGREGATES; COAGULATION; DYES; FLUORESCENCE; GELATION; GELS; TOLUENE;

AGGREGATE MORPHOLOGY; COMPLEX MOLECULES; FLUORESCENCE SPECTRA; GEL FORMATION; GELATION TEMPERATURE; LAYERED STRUCTURES; MOLECULAR PACKING STRUCTURE; ORGANOGELS; PERYLENE; PERYLENES; SOLUTION CONCENTRATION; TEM CHARACTERIZATION; XRD;

CATIONIC SURFACTANTS;

ACID; CATIONIC SURFACTANT; PERYLENE; PERYLENETETRACARBOXYLIC TETRAACID; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL; CRYSTALLIZATION; FLUORESCENT ORGANOGEL; GEL; GELATION; MOLECULE; MORPHOLOGY; PRIORITY JOURNAL; SOLUTION AND SOLUBILITY; TEMPERATURE; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 78751623196     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2010.11.080     Document Type: Article

References (55)

1. Flory P.J. Introductory lecture. Faraday Discuss. Chem. Soc. 1974, 57:7-18.
2. Estroff L.A., Hamilton A.D. Water gelation by small organic molecules. Chem. Rev. 2004, 104:1201-1217.
3. Banerjee S., Das R.K., Maitra U. Supramolecular gels 'in action'. J. Mater. Chem. 2009, 19:6649-6687.
4. Sangeetha N.M., Maitra U. Supramolecular gels: functions and uses. Chem. Soc. Rev. 2005, 34:821-836.
5. Terech P., Weiss R.G. Low molecular mass gelators of organic liquids and the properties of their gels. Chem. Rev. 1997, 97:3133-3159.
6. Abdallah D.J., Weiss R.G. Organogels and low molecular mass organic gelators. Adv. Mater. 2000, 12:1237-1247.
7. Weiss R.G., Terech P. Molecular Gels. Materials with Self-assembled Fibrillar Networks 2006, Springer, Dordrecht.
8. Bommel K.J.C., Friggeri A., Shinkai S. Organic templates for the generation of inorganic materials. Angew. Chem. Int. Ed. 2003, 42:980-999.
9. Hirst A.R., Escuder B., Miravet J.F., Smith D.K. High-tech applications of self-assembling supramolecular nanostructured gel-phase materials: from regenerative medicine to electronic devices. Angew. Chem. Int. Ed. 2008, 47:8002-8018.
10. Llusar M., Sanchez C. Inorganic and hybrid nanofibrous materials templated with organogelators. Chem. Mater. 2008, 20:782-820.
11. Ajayaghosh A., Praveen V.K., Vijayakumar C. Organogels as scaffolds for excitation energy transfer and light harvesting. Chem. Soc. Rev. 2008, 37:109-122.
12. Loos M., Feringa B.L., van Esch J.H. Design and application of self-assembled low molecular weight hydrogels. Eur. J. Org. Chem. 2005, 3615-3631.
13. Vintiloiu A., Leroux J.C. Organogels and their use in drug delivery-a review. J. Control. Release 2008, 125:179-192.
14. Zhu P.L., Yan X.H., Su Y., Yang Y., Li J.B. Solvent-induced structural transition of self-assembled dipeptide: from organogels to microcrystals. Chem. Eur. J. 2010, 16:3176-3183.
15. Yan X.H., Cui Y., He Q., Wang K.W., Li J.B. Organogels based on self-assembly of diphenylalanine peptide and their application to immobilize quantum dots. Chem. Mater. 2008, 20:1522-1526.
16. Schenning A.P.H.J., Meijer E.W. Supramolecular electronics; nanowires from self-assembled p-conjugated systems. Chem. Commun. 2005, 3245-3258.
17. Ajayaghosh A., Praveen V.K. π-Organogels of self-assembled p-phenylenevinylenes: soft materials with distinct size, shape, and functions. Acc. Chem. Res. 2007, 40:644-656.
18. Yagai S., Kubota S., Iwashima T., Kishikawa K., Nakanishi T., Karatsu T., Kitamura A. Supramolecular polymerization and polymorphs of oligo(p-phenylene vinylene)-functionalized bis- and monoureas. Chem. Eur. J. 2008, 14:5246-5257.
19. Oukachmih M., Destruel P., Seguy I., Ablart G., Jolinat P., Archambeau S., Mabiala M., Fouet S., Bock H. New organic discotic materials for photovoltaic conversion. Solar Energy Mater. Solar Cells 2005, 85:535-543.
20. Briseno A.L., Mannsfeld S.C.B., Reese C., Hancock J.M., Xiong Y., Jenekhe S.A., Bao Z., Xia Y. Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters. Nano Lett. 2007, 7:2847-2853.
21. Jones B.A., Facchetti A., Wasielewski M.R., Marks T.J. Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport. J. Am. Chem. Soc. 2007, 129:15259-15278.
22. Hoeben F.J.M., Jonkheijm P., Meijer E.W., Schenning A.P.H.J. About supramolecular assemblies of π-conjugated systems. Chem. Rev. 2005, 105:1491-1546.
23. Würthner F., Thalacker C., Diele S., Tschierske C. Fluorescent J-type aggregates and thermotropic columnar mesophases of perylene bisimide dyes. Chem. Eur. J. 2001, 7:2245-2253.
24. Chen Z., Stepanenko V., Dehm V., Prins P., Siebbeles L.D.A., Seibt J., Marquetand P., Engel V., Würthner F. Photoluminescence and conductivity of self-assembled π-π stacks of perylene bisimide dyes. Chem. Eur. J. 2007, 13:436-449.
25. Nolde F., Pisula W., Müller S., Kohl C., Müllen K. Synthesis and self-organization of core-extended perylene tetracarboxdiimides with branched alkyl substituents. Chem. Mater. 2006, 18:3715-3725.
26. Quante H., Geerts Y., Müllen K. Synthesis of soluble perylenebisamidine derivatives. Novel long-wavelength absorbing and fluorescent dyes. Chem. Mater. 1997, 9:495-500.
27. Würthner F., Sautter A., Schilling J. Synthesis of diazadibenzoperylenes and characterization of their structural, optical, redox, and coordination properties. J. Org. Chem. 2002, 67:3037-3044.
28. Kohl C., Weil T., Qu J., Müllen K. Towards highly fluorescent and water-soluble perylene dyes. Chem. Eur. J. 2004, 10:5297-5310.
29. Würthner F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem. Commun. 2004, 1564-1579.
30. Luca G.D., Liscio A., Maccagnani P., Nolde F., Palermo V., Müllen K., Samorì P. Nucleation-governed reversible self-assembly of an organic semiconductor at surfaces: long-range mass transport forming giant functional fibers. Adv. Funct. Mater. 2007, 17:3791-3798.
31. Balakrishnan K., Datar A., Naddo T., Huang J., Oitker R., Yen M., Zhao J., Zang L. Effect of side-chain substituents on self-assembly of perylene diimide molecules: morphology control. J. Am. Chem. Soc. 2006, 128:7390-7398.
32. Herrikhuyzen J., Syamakumari A., Schenning A.P.H.J., Meijer E.W. Synthesis of n-type perylene bisimide derivatives and their orthogonal self-assembly with p-type oligo(p-phenylene vinylene)s. J. Am. Chem. Soc. 2004, 126:10021-10027.
33. Thalacker C., Würthner F. Chiral perylene bisimide-melamine assemblies: hydrogen bond-directed growth of helically stacked dyes with chiroptical properties. Adv. Funct. Mater. 2002, 12:209-218.
34. Yagai S., Seki T., Karatsu T., Kitamura A., Würthner F. Transformation from H- to J-aggregated perylene bisimide dyes by complexation with cyanurates. Angew. Chem. Int. Ed. 2008, 47:3367-3371.
35. Schenning A.P.H.J., Herrikhuyzen J., Jonkheijm P., Chen Z., Würthner F., Meijer E.W. Photoinduced electron transfer in hydrogen-bonded oligo(p-phenylene vinylene)-perylene bisimide chiral assemblies. J. Am. Chem. Soc. 2002, 124:10252-10253.
36. Würthner F., Chen Z., Hoeben F.J.M., Osswald P., You C., Jonkheijm P., Herrikhuyzen J., Schenning A.P.H.J., Schoot P.P.A.M., Meijer E.W., Beckers E.H.A., Meskers S.C.J., Janssen R.A.J. Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes. J. Am. Chem. Soc. 2004, 126:10611-10618.
37. Laiho A., Smarsly B.M., Faul C.F.J., Ikkala O. Macroscopically aligned ionic self-assembled perylene-surfactant complexes within a polymer matrix. Adv. Funct. Mater. 2008, 18:1890-1897.
38. Guan Y., Yu S., Antonietti M., Bçttcher C., Faul C.F.J. Synthesis of supramolecular polymers by ionic self-assembly of oppositely charged dyes. Chem. Eur. J. 2005, 11:1305-1311.
39. Datar A., Oitker R., Zang L. Surface-assisted one-dimensional self-assembly of a perylene based semiconductor molecule. Chem. Commun. 2006, 1649-1651.
40. Wang W., Li L., Helms G., Zhou H., Li A.D.Q. To fold or to assemble. J. Am. Chem. Soc. 2003, 125:1120-1121.
41. Balakrishnan K., Datar A., Oitker R., Chen H., Zuo J., Zang L. Nanobelt self-assembly from an organic n-type semiconductor: propoxyethyl-PTCDI. J. Am. Chem. Soc. 2005, 127:10496-10497.
42. Che Y., Datar A., Yang X., Naddo T., Zhao J., Zang L. Enhancing one-dimensional charge transport through intermolecular π-electron delocalization: conductivity improvement for organic nanobelts. J. Am. Chem. Soc. 2007, 129:6354-6355.
43. Zhang X., Chen Z., Würthner F. Morphology control of fluorescent nanoaggregates by co-self-assembly of wedge- and dumbbell-shaped amphiphilic perylene bisimides. J. Am. Chem. Soc. 2007, 129:4886-4887.
44. Che Y., Datar A., Balakrishnan K., Zang L. Ultralong nanobelts self-assembled from an asymmetric perylene tetracarboxylic diimide. J. Am. Chem. Soc. 2007, 129:7234-7235.
45. Chen Z., Lohr A., Sara-Möller C.R., Würthner F. Self-assembled p-stacks of functional dyes in solution: structural and thermodynamic features. Chem. Soc. Rev. 2009, 38:564-584.
46. Ghosh S., Li X., Stepanenko V., Würthner F. Control of H- and J-type p stacking by peripheral alkyl chains and self-sorting phenomena in perylene bisimide homo- and heteroaggregate. Chem. Eur. J. 2008, 14:11343-11357.
47. Li X., Stepanenko V., Chen Z., Prins P., Siebbeles L.D.A., Würthner F. Functional organogels from highly efficient organogelator based on perylene bisimide semiconductor. Chem. Commun. 2006, 3871-3873.
48. Li X.Q., Zhang X., Ghosh S., Würthner F. Highly fluorescent lyotropic mesophases and organogels based on J-aggregates of core-twisted perylene bisimide dyes. Chem. Eur. J. 2008, 14:8074-8078.
49. Sugiyasu K., Fujita N., Shinkai S. Visible-light-harvesting organogel composed of cholesterol-based perylene derivatives. Angew. Chem. Int. Ed. 2004, 43:1229-11229.
50. Fu G., Wang M., Wang Y., Xia N., Zhang X., Yang M., Zheng P., Wang W., Burger C. Ionic self-assembled derivatives of perylenetetracarboxylic dianhydride: facile synthesis, morphology and structures. New J. Chem. 2009, 33:784-792.
51. Jancy B., Asha S.K. Hydrogen-bonding-induced conformational change from J to H aggregate in novel highly fluorescent liquid-crystalline perylenebisimides. Chem. Mater. 2008, 20:169-181.
52. Debije M.G., Chen Z., Piris J., Neder R.B., Watson M.M., Müllen K., Würthner F. Dramatic increase in charge carrier lifetime in a liquid crystalline perylene bisimide derivative upon bay substitution with chlorine. J. Mater. Chem. 2005, 15:1270-1276.
53. Chen Z., Baumeister U., Tschierske C., Würthner F. Effect of core twisting on self-assembly and optical properties of perylene bisimide dyes in solution and columnar liquid crystalline phases. Chem. Eur. J. 2007, 13:450-465.
54. Fink R.F., Seibt J., Engel V., Renz M., Kaupp M., Lochbrunner S., Zhao H.-M., Pfister J., Würthner F., Engels B. Exciton trapping in π-conjugated materials: a quantum-chemistry-based protocol applied to perylene bisimide dye aggregates. J. Am. Chem. Soc. 2008, 130:12858-12859.
55. Stevens B., Ban M.I. Spectrophotometric determination of enthalpies and entropies of photoassociation for dissolved aromatic hydrocarbons. Trans. Faraday Soc. 1964, 60:1515-1523.