Cycloparaphenylene as a molecular porous carbon solid with uniform pores exhibiting adsorption-induced softness

Sakamoto, Hirotoshi; Fujimori, Toshihiko; Li, Xin; Kaneko, Katsumi; Kan, Kai; Ozaki, Noriaki; Hijikata, Yuh; Irle, Stephan; Itami, Kenichiro

doi:10.1039/c6sc00092d

Cited by 56 publications

(100 citation statements)

References 87 publications

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“…Thep resent study is built upon our discovery that structural distortions of aC PP crystal occur with the application of electric stimulus.C PP,w hich forms uniform channels in the solid state (see Figure S1 in the Supporting Information), [9,10] showed structural distortions caused by electric stimulus application with the stacking mode of CPP being preserved ( Figure S2). …”

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confidence: 99%

“…[11] This led to the even more exciting discovery that the thus-formed [10]CPP-iodine assembly ( [10]CPP-I) showed turn-on electronic conductivity and white light luminescence upon voltage bias application. To uncover the ring-size effect, [9]CPP-I and [12]CPP-I were also prepared and investigated.…”

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confidence: 99%

“…[9] Moreover,C PP represents an ew carbon-based soft porous material with unique adsorption behaviors,directly related to the intrinsic hollow nanospace in the solid state. [10] CPP-based porous frameworks can confine only molecules that fit the specific pore size.P recise control of the number and alignment of confined molecules is realized by changing the number of benzene rings of [n]CPP,m aking it possible to explore the proper combinations to show cooperative changes in structure and properties.…”

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confidence: 99%

“…[12] In the CPP pores,I 2 molecules were periodically accommodated in ac ommensurate fashion with their crystal lattices (Figure 2a,b). Tw oI 2 molecules were encapsulated per [9]CPP and [10]CPP molecule,a nd four I 2 molecules in each [12]CPP molecule.T he electron density of the iodine atoms is more delocalized in [10]CPP and [12]CPP rings than in [9]…”

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confidence: 99%

“…Single crystals of [9]CPP-I, [10]CPP-I,a nd [12]CPP-I were prepared by concentrating mixed solution of CPPs and iodine to dryness (Scheme S1). Them olecular structures of these assemblies were successfully obtained by X-ray crystallography ( Figure 2a nd Table S1), with their electron density maps derived by the maximum entropy method (MEM).…”

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Numerous otherwise difficult applications have been realized with materials, the chemical/physical properties of which can be controlled by external stimuli such as heat, pressure, photo‐irradiation, and voltage bias. However, the complexity of design and the lack of easy‐to‐conduct synthetic methods make the creation of on‐demand stimuli responsive materials a formidable task. Here we report an electric‐stimuli‐responsive multifunctional material, [10]CPP‐I: crystalline assembly of a hydrocarbon nanoring ([10]cycloparaphenylene: [10]CPP) as an “electro‐responsive porous host” and iodine as a “potentially functional molecule”. Through applying electric stimulus, [10]CPP‐I turned to exhibit two attractive properties: electronic conductivity and white light emission. We revealed that electric stimuli trigger the cascade formation of polyiodide chains inside the [10]CPP assembly through charge transfer, leading to the emergence of these properties. This “responsive porous host” approach is expected to be applicable for different stimuli, and opens the path for devising a generic strategy to the development of stimuli‐responsive materials.

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Electrically Activated Conductivity and White Light Emission of a Hydrocarbon Nanoring–Iodine Assembly

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Carbon Nanorings and Nanobelts: Material Syntheses, Molecular Architectures, and Applications

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Carbon nanorings (CNRs) and carbon nanobelts (CNBs) of various sizes and innovative molecular architectures have ushered improvement in research in recent years. This serves as a prerequisite for further advances and applications, such as organic semiconductors and bottom‐up synthesis of single‐walled carbon nanotubes. Nevertheless, challenges such as high strain energy, excessive reactivity, end‐product stability, low‐scale yields, and side reactions inhibit material synthesis and applications. In this review, CNRs, CNBs, and other heteroatom‐doped molecular belts are discussed based on their molecular structural characteristics, with a special focus on their developments in the past two years. Furthermore, current applications, research obstacles, and future developments related to CNRs and CNBs are discussed. For the first time, studies and advancements in organic field‐effect transistors (OFETs) have been summarized in detail.

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[4]‐Cyclo‐2,7‐Carbazole as Host Material in High‐Efficiency Phosphorescent OLEDs: A New Perspective for Nanohoops in Organic Electronics

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In the last ten years, the development of -conjugated nanohoops has been considerable owing to their remarkable properties. However, to date, their incorporation in organic electronic devices remains very scarce. In this work, we report the first high performance organic electronic device (i.e. Phosphorescent Organic Light-Emitting Diode PhOLED) incorporating a nanohoop ([4]-cyclo-N-butyl-2,7-carbazole [4]C-Bu-Cbz), revealing their potential in electronics. Thus, using the red phosphor Ir(MDQ) 2 (acac), the [4]C-Bu-Cbz-based PhOLED displays a high External Quantum Efficiency (EQE) of 17.0 %, a Current Efficiency (CE) of 20.6 cd.A -1 and a Power Efficiency (PE) of 25.8 lm.W -1 demonstrating that the charges injection, transport and recombination are particularly efficient. This performance is significantly higher than that of its linear counterpart, N-butyl-2,7quartercarbazole [4]L-Bu-Cbz, which presents an EQE of 11.1 %, a CE of 13.0 cd.A -1 and a PE of 15.7 lm.W -1 . The significant difference, in term of device performance, between cyclic and acyclic compounds provides a new basis to construct high-performance electronic devices. This study, which includes optical, electrochemical, morphological and charge transport properties, shows that nanohoops can be efficiently used as organic semi-conductors in electronics and opens the way to their practical uses in highperformance optoelectronic devices, which is now the next stage of their evolution.

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Cycloparaphenylene as a molecular porous carbon solid with uniform pores exhibiting adsorption-induced softness

Abstract: The molecular carbon nanoring, cycloparaphenylene (CPP), is fascinating as a new class of carbonaceous porous solids with the uniform structure of an all-benzene surface.

Cited by 56 publications

References 87 publications

Electrically Activated Conductivity and White Light Emission of a Hydrocarbon Nanoring–Iodine Assembly

Electrically Activated Conductivity and White Light Emission of a Hydrocarbon Nanoring–Iodine Assembly

Carbon Nanorings and Nanobelts: Material Syntheses, Molecular Architectures, and Applications

[4]‐Cyclo‐2,7‐Carbazole as Host Material in High‐Efficiency Phosphorescent OLEDs: A New Perspective for Nanohoops in Organic Electronics

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