Self-assembly constructed by perylene bisimide derivatives bearing complementary hydrogen-bonding moieties

Abstract

An intermediate compound 2, 4-bis(laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, 3, 5-triazine was prepared by stepwise nucleophilic substitution on triazine ring by lauryl amine and subsequently 1-(2-aminoethyl)-piperazine. Then imidization of perylene-3, 4, 9, 10-tetracarboxylic acid dianhydride with 2,4-bis(laurylamino)-6-(1-(2-aminoethyl)-piperazine)-1, 3, 5-triazine was carried out to afford a novel perylene derivative bearing two melamine blocks (S₂) and 1, 6, 7, 12-tetra(4-tert-butyl phenoxy)-perylene-3, 4, 9, 10-tetracarboxylic acid bisimide (S₁). The hydrogen-bonding interactions between S₁ and S₂ were investigated by ¹H NMR spectrum, UV/Vis spectrum and fluorescence spectrum. The influences on the morphologies of S₁·S₂ aggregates were investigated. The results show that well-defined nanofibers with a diameter of about 100 nm can be obtained by self-assembly between S₁ and S₂ only in CH₂Cl₂ solution. Based on these results, guidelines for the molecular design and self-assembly of supramolecular polymer materials are presented.

Keywords

perylene bisimide / self-assembly / hydrogen-bonding / synthesis

References

[1] BrunsveldL., FolmerB. J. B., MeijerE. W., SijbesmaR. P.. Supramolecular polymer [J]. Chem Rev, 2001, 101(12): 4071-4097

[2] HoebenF. J. M., JonkheijmP., MeijerE. W., SchenningA. P. H. J.. About supramolecular assemblies of π-conjugated systems [J]. Chem Rev, 2005, 105(4): 1491-1546

[3] OualiL., KrasnikovV. V., StalmachU.. Oligo(phenylenevinylene)/fullerene photovoltaic cells: Influence of morphology [J]. Adv Mater, 1999, 11(14): 1515-1518

[4] WürthnerF., ThalackerC., SautterA., SchärtlW., IbachW., HollricherO.. Hierarchical self-organization of perylene bisimide-melamine assemblies to fluorescent mesoscopic superstructures [J]. Chem Eur J, 2000, 6(21): 3871-3886

[5] ZhangJ., HoebenF. J. M., PouderoijenM. J., SchenningA. P. H. J., MeijerE. W., de SchryverF. C., de FeyterS.. Hydrogen-bonded oligo(p-phenylenevinylene) functionalized with perylene bisimide: Self-assembly and energy transfer [J]. Chem Eur J, 2006, 12(35): 9046-9055

[6] WangY., ChenY., LiR., WangS., SuW., MaP., WasielewskiM. R.. Amphiphilic perylenetretracarboxyl diimide dimer and its application in field effect transistor [J]. Langmuir, 2007, 23(10): 5836-5842

[7] MoriuchiT., TamuraT., HiraoT.. Self-assembly of dipeptidyl ureas: A new class of hydrogen-bonded molecular duplexes [J]. J Am Chem Soc, 2002, 124(32): 9356-9357

[8] YagaiS., KaratsuT., KitamuraA.. Binary supramolecular gels based on bismelamine cyanurate/barbiturate noncovalent polymers [J]. Chem Mater, 2004, 16(19): 3582-3585

[9] DefeytarS., WürthnerF., MeijerE. W., ShengY., ZhigianC., WurthnerF.. Two-dimensional self-assembly into multicomponent hydrogen-bonded nanostructures [J]. Nano Lett, 2005, 5(1): 77-81

[10] YagaiS., MonmaY., KawauchiN., KarastyT., Kitawuraa. Supramolecular nanoribbons and nanoropes generated from hydrogen-bonded supramolecular polymers containing perylene bisimide chromophores [J]. Org Lett, 2007, 9(6): 1137-1140

[11] WÜRTHNER F. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures [J]. Chem Commun, 2004(14): 1564–1579.

[12] SinksL. E., RybtchinskiB., LimuraM., JuvesB. A., GosheA. T.. Self-assembly of photofunctional cylindrical nanostructures based on perylene-3, 4, 9, 10-bis(dicarboximide) [J]. Chem Mater, 2005, 17(25): 6295-6303

[13] WürthnerF., ThalackerC., SautterA.. Hierarchical organization of functional perylene chromophores to mesoscopic superstructures by hydrogen bonding and π-π interactions [J]. Adv Mater, 1999, 11(9): 754-758

[14] LiuY., ZhuangJ., LiuH., LiY., LuF., GanH., JiuT.. Self-assembly and characterization of hydrogen-bond-induced nanostructure [J]. Chem Phys Chem, 2004, 5(8): 1210-1215

[15] LiuY., XiaoS., ZhuD., ZhuangJ., LuF., LiY., XiaoS.. Self-assembly and characterization of a novel hydrogen-bonded nanostructure [J]. J Phys Chem B, 2004, 108(20): 6256-6260

[16] ThalackerC., WürthnerF.. Chiral perylene bisimide-melamine assemblies: Hydrogen bond-directed growth of helically stacked dyes with chiroptical properties [J]. Adv Funct Mater, 2002, 12(3): 209-218

[17] YangX.-g., SunJ.-z., LiH.-y., CaoJ., WangM.. Fluorescence switch based on a porphyrin-perylenediimde dyad [J]. Chinese Chemical Letters, 2005, 16(2): 257-260

[18] XieB.-y., CaoY.-f., SunJ.-z., YangX.-g., WangM.. Change in aggregation state of a porphyrin-perylene-diimide dyad induced by trifluoroacetic acid [J]. Chinese Science Bulletin, 2007, 52(19): 2266-2270

[19] SteffensenM. B., SimanekE. E.. Chemoselective building blocks for dendrimers from relative reactivity data [J]. Org Lett, 2003, 5(13): 2359-2361

[20] PrinsL. J., ReinhoudtD. N., TimmeermanP.. Non-covalent synthesis using hydrogen bonding [J]. Angew Chem Int Ed, 2001, 123(40): 2383-2426

[21] MessmoreB. W., HulvatJ. F., SoneE. D., StuppS. I.. Synthesis, Self-assembly, and characterization of supramolecular polymers from electroactive dendron rodcoil molecules [J]. Am Chem Soc, 2004, 126(44): 14452-14458

[22] PraveenV. K., GeorgeS. J., VargheseR., VijayakumarC., AjayaghoshA.. Self-Assembled π-nanotapes as donor scaffolds for selective and thermally gated fluorescence resonance energy transfer (FRET) [J]. Am Chem Soc, 2006, 128(23): 7542-7550

[23] GuerzoA. D., OliveA. G. L., ReichwagenJ., HopfH., DesvergneJ. P.. Energy transfer in self-assembled [n]-acene fibers involving ≥100 donors per acceptor [J]. Am Chem Soc, 2005, 127(51): 17984-17985