Application of Photochemistry in Regulation and Exploration in Molecular Self-assembly

doi:10.7517/j.issn.1674-0475.2015.01.015

Abstract

Abstract:

Photochemical changes which induced by light irradiation is an ideal method to provide energy and external stimuli to microscopic systems via macroscopic means. This method is plays an important role in the research area of molecular self-assembly. By using photochemical methods multi-level regulation to the molecular self-assemblies can be realized from molecular level to microscopic structure, and finally macroscopic properties. On the other hand, the luminescence of aggregates can be controlled by regulating the assembly structure and the molecular arrangement via other methods. After all, molecular fluorescence probes provide vigorous supports to explore the imformations of the nanometer-scaled molecular self-assemblies which is an important method in research of self-assembled structures. In this paper, we review the above areas of application of photochemical methods in regulation and exploration of molecular self-assembly and the aggregate structure-related luminescence changes.

Key words: self-assembly, photochemistry, fluorescentprobe, regulation of self-assemly structure

WANG Andong, YAN Yun, HUANG Jianbin. Application of Photochemistry in Regulation and Exploration in Molecular Self-assembly[J]. Imaging Science and Photochemistry, 2015, 33(1): 15-27.

References

[1] Whitesides G M, Mathias J P, Seto C T. Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures[J]. DTIC Document, 1991.
[2] Whitesides G M, Grzybowski B. Self-assembly at all scales[J]. Science, 2002, 295: 2418-2421.
[3] Philp D, Stoddart J F. Self-assembly in natural and unnatural systems[J]. Angewandte Chemie International Edition in English, 1996, 35:1154-1196.
[4] Stupp S I, LeBonheur V, Walker K, Li L-S, Huggins K E, Keser M, Amstutz A. Supramolecular materials: self-organized nanostructures[J]. Science, 1997, 276: 384-389.
[5] Aida T, Meijer E W, Stupp S I, Functional supramolecular polymers[J]. Science, 2012, 335: 813-817.
[6] Israelachvili J, Pashley R.The hydrophobic interaction is long range, decaying exponentially with distance[J]. Nature, 1982, 300: 341-342.
[7] Hartgerink J D, Beniash E, Stupp S I. Self-assembly and mineralization of peptide-amphiphile nanofibers[J]. Science, 2001, 294: 1684-1688.
[8] Jiang L X, Deng M L, Wang Y L, Liang D H, Yan Y, Huang J B.Special effect of β-cyclodextrin on the aggregation behavior of mixed cationic/anionic surfactant systems[J]. The Journal of Physical Chemistry B, 2009, 113:7498-7504.
[9] Willerich I, Gröhn F. Photoswitchable nanoassemblies by electrostatic self-assembly[J]. Angewandte Chemie International Edition, 2010, 49: 8104-8108.
[10] Ranganathan D, Haridas V, Gilardi R, Karle I L. Self-assembling aromatic-bridged serine-based cyclodepsipeptides (serinophanes): a demonstration of tubular structures formed through aromatic π-π interactions[J]. Journal of the American Chemical Society, 1998, 120: 10793-10800.
[11] Mynar J L, Yamamoto T, Kosaka A, Fukushima T, Ishii N, Aida T.Radially diblock nanotube: Site-selective functionalization of a tubularly assembled hexabenzocoronene[J]. Journal of the American Chemical Society, 2008, 130:1530-1531.
[12] Yan Y, Besseling N A, de Keizer A, Marcelis A, Drechsler M, Stuart C, Martien A. Hierarchical self-assembly in solutions containing metal ions, ligand, and diblock copolymer[J]. Angewandte Chemie International Edition, 2007, 46:1807-1809.
[13] Ercole F, Davis T P, Evans R A. Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond[J]. Polymer Chemistry, 2010, 1:37-54.
[14] Hong Y, Lam J W, Tang B Z.Aggregation-induced emission[J]. Chemical Society Reviews, 2011, 40: 5361-5388.
[15] Sagara Y, Yamane S, Mutai T, Araki K, Kato T. A stimuli-responsive, photoluminescent, anthracene-based liquid crystal: emission color determined by thermal and mechanical processes[J]. Advanced Functional Materials, 2009, 19:1869-1875.
[16] An B-K, Gierschner J, Park S Y. π-Conjugated cyanostilbene derivatives.a unique self-assembly motif for molecular nanostructures with enhanced emission and transport[J]. Accounts of Chemical Research, 2011, 45: 544-554.
[17] Aida T, Meijer E, Stupp S. Functional supramolecular polymers[J]. Science, 2012, 335: 813-817.
[18] Li C H, Wu T, Hong C Y, Zhang G Q, Liu S Y. A general strategy to construct fluorogenic probes from charge-generation polymers (CGPs) and AIE-active fluorogens through triggered complexation[J]. Angewandte Chemie-International Edition, 2012, 51:455-459.
[19] Li D D, Liu J Z, Kwok R T K, Liang Z Q, Tang B Z, Yu J H. Supersensitive detection of explosives by recyclable AIE luminogen-functionalized mesoporous materials[J]. Chemical Communications, 2012, 48: 7167-7169.
[20] Germain M E, Knapp M J. Optical explosives detection: from color changes to fluorescence turn-on[J]. Chemical Society Reviews, 2009, 38: 2543-2555.
[21] Zhao L, Yan Y, Huang J B. Application of fluorescent probe technology in self-assembly systems of amphiphile aqueous solutions[J]. Acta Physico-Chimica Sinica, 2010, 26: 840-849.
[22] Liu N, Chen Z, Dunphy D R, Jiang Y B, Assink R A, Brinker C J. Photoresponsive nanocomposite formed by self-assembly of an azobenzene-modified silane[J]. Angewandte Chemie International Edition, 2003, 42:1731-1734.
[23] Grzelczak M, Vermant J, Furst E M, Liz-Marzán L M.Directed self-assembly of nanoparticles[J]. ACS nano, 2010, 4: 3591-3605.
[24] Wang D R, Wang X G. Amphiphilic azo polymers: molecular engineering, self-assembly and photoresponsive properties[J]. Progress in Polymer Science, 2013, 38: 271-301.
[25] Ohya Y, Okuyama Y, Fukunaga A, Ouchi T. Photo-sensitive lipid membrane perturbation by a single chain lipid having terminal spiropyran group[J]. Supramolecular Science,1998, 5:21-29.
[26] Samanta S, Locklin J. Formation of photochromic spiropyran polymer brushes via surface-initiated, ring-opening metathesis polymerization: reversible photocontrol of wetting behavior and solvent dependent morphology changes[J]. Langmuir, 2008, 24: 9558-9565.
[27] Sakai K, Imaizumi Y, Oguchi T, Sakai H, Abe M. Adsorption characteristics of spiropyran-modified cationic surfactants at the silica/aqueous solution interface[J]. Langmuir, 2010, 26: 9283-9288.
[28] Yamauchi K, Takashima Y, Hashidzume A, Yamaguchi H, Harada A.Switching between supramolecular dimer and nonthreaded supramolecular self-assembly of stilbene amide-α-cyclodextrin by photoirradiation[J]. Journal of the American Chemical Society, 2008, 130:5024-5025.
[29] Chen Z, He Y H, Wang Y, Wang X G. Amphiphilic diblock copolymer with dithienylethene pendants: synthesis and photo-modulated self-assembly[J]. Macromolecular Rapid Communications, 2011, 32: 977-982.
[30] Browne W R, Kudernac T, Katsonis N, Areephong J, Hjelm J, Feringa B L.Electro- and photochemical switching of dithienylethene self-assembled monolayers on gold electrodes[J]. The Journal of Physical Chemistry C, 2008, 112:1183-1190.
[31] Myles A J, Branda N R. 1, 2-Dithienylethene photochromes and non-destructive erasable memory[J]. Advanced Functional Materials, 2002, 12:167-173.
[32] Kumar G S, Neckers D. Photochemistry of azobenzene-containing polymers[J]. Chemical Reviews,1989, 89:1915-1925.
[33] Wang Y P, Ma N, Wang Z Q, Zhang X. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with α-cyclodextrin[J]. Angewandte Chemie International Edition, 2007, 46: 2823-2826.
[34] Lin Y Y, Cheng X H, Qiao Y, Yu C L, Li Z B, Yan Y, Huang J B. Creation of photo-modulated multi-state and multi-scale molecular assemblies via binary-state molecular switch[J]. Soft Matter, 2010, 6:902-908.
[35] Lin Y Y, Wang A D, Qiao Y, Gao C, Drechsler M, Ye J P, Yan Y, Huang J B. Rationally designed helical nanofibers via multiple non-covalent interactions: fabrication and modulation[J]. Soft Matter, 2010, 6: 2031-2036.
[36] Yan Y, Lin Y Y, Qiao Y, Huang J B. Construction and application of tunable one-dimensional soft supramolecular assemblies[J]. Soft Matter, 2011, 7: 6385-6398.
[37] Lin Y, Qiao Y, Gao C, Tang P, Liu Y, Li Z, Yan Y, Huang J. Tunable one-dimensional helical nanostructures: from supramolecular self-assemblies to silica nanomaterials[J]. Chemistry of Materials, 2010, 22:6711-6717.
[38] Lin Y Y, Qiao Y, Tang P F, Li Z B, Huang J B. Controllable self-assembled laminated nanoribbons from dipeptide-amphiphile bearing azobenzene moiety[J]. Soft Matter, 2011, 7:2762-2769.
[39] Minkin V I. Photo-, thermo-, solvato-, and electrochromic spiroheterocyclic compounds[J]. Chemical Reviews, 2004, 104: 2751-2776.
[40] Krongauz V, Goldburt E.Quasi-crystals from irradiated photochromic dyes in an applied electric field. 1978.
[41] Onai Y, Mamiya M, Kiyokawa T, Okuwa K, Kobayashi M, Shinohara H, Sato H.Colored merocyanine aggregates: long-lived crystals of large size (10-100. mu. m) and deaggregation of small aggregates in solutions[J]. The Journal of Physical Chemistry,1993, 97: 9499-9505.
[42] Alonso M, Reboto V, Guiscardo L, San Martin A, Rodriguez-Cabello J.Spiropyran derivative of an elastin-like bioelastic polymer: photoresponsive molecular machine to convert sunlight into mechanical work[J]. Macromolecules, 2000, 33:9480-9482.
[43] Chen Q, Feng Y, Zhang D Q, Zhang G X, Fan Q H, Sun S N, Zhu D B. Light-triggered self-assembly of a spiropyran-functionalized dendron into nano-/micrometer-sized particles and photoresponsive organogel with switchable fluorescence[J]. Advanced Functional Materials, 2010, 20: 36-42.
[44] Wang C, Chen Q S, Xu H P, Wang Z Q, Zhang X. Photoresponsive supramolecular amphiphiles for controlled self-assembly of nanofibers and vesicles[J]. Advanced Materials, 2010, 22: 2553-2555.
[45] Wang C, Wang Z Q, Zhang X. Amphiphilic building blocks for self-assembly: from amphiphiles to supra-amphiphiles[J]. Accounts of Chemical Research, 2012, 45:608-618.
[46] Zhang X, Wang C. Supramolecular amphiphiles[J]. Chemical Society Reviews, 2011, 40:94-101.
[47] Han P, Li S C, Wang C, Xu H P, Wang Z Q, Zhang X, Thomas J, Smet M. UV-responsive polymeric superamphiphile based on a complex of malachite green derivative and a double hydrophilic block copolymer[J]. Langmuir, 2011, 27: 14108-14111.
[48] Benrraou M, Bales B L, Zana R. Effect of the nature of the counterion on the properties of anionic surfactants. 1. Cmc, ionization degree at the cmc and aggregation number of micelles of sodium, cesium, tetramethylammonium, tetraethylammonium, tetrapropylammonium, and tetrabutylammonium dodecyl sulfates[J]. Journal of Physical Chemistry B, 2003, 107: 13432-13440.
[49] Balter A, Nowak W, Pawelkiewicz W, Kowalczyk A.Some remarks on the interpretation of the spectral properties of prodan[J]. Chemical Physics Letters,1988, 143: 565-570.
[50] Kalyanasundaram K, Thomas J K.Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems[J]. Journal of the American Chemical Society,1977, 99: 2039-2044.
[51] Huang J B, Zhao G X. Fluorescence probes study on the mixed cationic-anionic surfactant solutions[J]. Colloid and Polymer Science, 1996, 274: 747-753.
[52] Mukherjee S, Chattopadhyay A. Influence of ester and ether linkage in phospholipids on the environment and dynamics of the membrane interface: a wavelength-selective fluorescence approach[J]. Langmuir, 2005, 21:287-293.
[53] Yin H Q, Lin Y Y, Huang J B. Microstructures and rheological dynamics of viscoelastic solutions in a catanionic surfactant system[J]. Journal of Colloid and Interface Science, 2009, 338:177-183.
[54] Yao J X, Zhao Y, Huang J B.Multivalent metal ion induced vesicle aggregation in aqueous polyelectrolyte-surfactant system[J]. Acta Physico-Chimica Sinica, 2006, 22: 913-916.
[55] Zhao Y, Yan Y, Jiang L X, Huang J B, Hoffmann H. Phase and self-assembly transition induced by glycerol-borax interaction in an aqueous surfactant two-phase system[J]. Soft Matter, 2009, 5:4250-4255.
[56] Gao L N, Song Q, Huang X, Huang J B. A new surfactant-fluorescence probe for detecting shape transitions in self-assembled systems[J]. Journal of Colloid and Interface Science, 2008, 323:420-425.
[57] Gao L N, Zhao L, Huang X, Xu B C, Yan Y, Huang J B. A surfactant type fluorescence probe for detecting micellar growth[J]. Journal of Colloid and Interface Science, 2011, 354: 256-260.
[58] Bergström M, Pedersen J S, Schurtenberger P, Egelhaaf S U. Small-angle neutron scattering (SANS) study of vesicles and lamellar sheets formed from mixtures of an anionic and a cationic surfactant[J]. The Journal of Physical Chemistry B,1999, 103:9888-9897.
[59] Hong Y N, Lam J W Y, Tang B Z. Aggregation-induced emission: phenomenon, mechanism and applications[J]. Chemical Communications, 2009, 4332-4353.
[60] Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Hoi Sing Kwok, Zhan X W, Liu Y Q, Zhu D B, Tang B Z. Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole[J]. Chemical Communications, 2001, 1740-1741.
[61] Dong R J, Zhu B S, Zhou Y F, Yan D Y, Zhu X Y. "Breathing" Vesicles with Jellyfish‐like On-Off Switchable Fluorescence Behavior[J]. Angewandte Chemie International Edition, 2012, 51:11633-11637.
[62] Yu H Q, Liao D W, Johnston M B, Li B J. All-optical full-color displays using polymer nanofibers[J]. ACS Nano, 2011, 5:2020-2025.
[63] He G J, Guo D, He C, Zhang X L, Zhao X W, Duan C Y. A color-tunable europium complex emitting three primary colors and white light[J]. Angewandte Chemie International Edition, 2009, 48: 6132-6135.
[64] Zhao L, Jiang L X, Han Y C, Xian Z Y, Huang J B, Yan Y. A case of cyclodextrin-catalyzed self-assembly of an amphiphile into microspheres[J]. Soft Matter, 2013, 9:7710-7717.
[65] Zhao L, Cheng X H, Ding Y, Yan Y, Huang J B. A surfactant-assisted unimolecular platform for multicolor emissions[J]. Soft Matter, 2012, 8:10472-10478.