Polycyclic aromatic hydrocarbons (PAHs) are excellent building blocks for the creation of two-dimensional (2D) nanosheets.However,large PAHs tend to exhibit poor or no solubility in organic solvents and water.T oo vercome this issue,w ee mployed water-soluble micellar capsules consisting of V-shaped amphiphilic molecules.C haracteristic electrochemical behavior was observed in 0.1m H 2 SO 4 in the presence of the water-soluble capsules containing PAHs,s uch as ovalene,c ircobiphenyl, and dicoronylene.F urthermore, under these conditions,P AHs were released from the capsules, resulting in the formation of a2 Da dlayer of PAHs at the electrochemical interface.F inally,u sing electrochemical scanning tunneling microscopy, we demonstrate that our molecular containers based on water-soluble molecular capsules allowthe facile preparation of 2D PAHa dlayers in addition to structurally controlling nanostructure formation on Au surfaces.Carbon materials,s uch as graphene,h ave been extensively studied for their application in electronic devices, [1][2][3] photodetectors, [4][5][6] capacitors, [7] electrocatalysis, [8][9][10] and sensors. [11] Similarly,p olycyclic aromatic hydrocarbons (PAHs) with planar structures exhibit excellent donor abilities owing to their p-conjugated structures.A ss uch, PA Hs are promising materials for use as two-dimensional (2D) nanoarchitectures, such as "nanographene", which should create novel functionalities for electronic devices,i ncluding electrochromic devices [1,12] and quantum dots. [13] Fore xample,f unctionalized graphene quantum dots that allow the control of band gaps indicate the structural dependence of photocatalysts in water splitting and carbon dioxide reduction under visible-light irradiation. [13] Indeed, to date,anumber of attractive PA Hs have been synthesized by the Müllen group. [1, 12,14] Thedesign and synthesis of structurally defined PA Hs are essential for the creation of functional graphenes based on elemental doping and periodical defects (or vacancies) as the building blocks.However,large PA Hs without peripheral substituents are insoluble in both water and organic solvents.T he formation of adlayers on electrode surfaces is challenging because PA Hs without peripheral substituents are used as 2D molecular templates, [15] have applications in conductance enhancement between nanographene and Au junctions, [16] and are used in organic field-effect transistors (OFETs). [17] In contrast, the V-shaped amphiphilic molecule 1 (Scheme 1) forms micellar capsules (1) n in water and solubilizes various water-insoluble compounds.I np articular, p-conjugated planar molecules,s uch as metalloporphyrins,p hthalocyanines,p entacenes,a nd coronenes,h ave been applied for this purpose. [18,19] We report herein water-soluble molecular capsules consisting of V-shaped amphiphilic molecules for the uptake of large PA Hs (i.e., ovalene,c ircobiphenyl, and dicoronylene; Scheme 1). In this study,w ea lso examined the electrochemical behavior of the PA H-containing molecular capsules an...

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Unlike common polyaromatic hydrocarbons, acridine is a characteristic compound bearing both π-stackable large surfaces and a protonable nitrogen atom. Here we report the first synthesis of a supramolecular capsule with multiple acridine panels. In water, the assembly and disassembly of the capsule reversibly occur under neutral and acidic conditions, respectively (≥10 cycles). Notably, the pH-responsive capsule encapsulates a variety of large hydrophobic compounds (up to 1.6 nm in diameter) such as coumarins, metallophthalocyanines and subphthalocyanine in neutral water and subsequently releases them by simple addition of acid.