Separation of Linear and Branched Alkanes Using Host–Guest Complexation of Cyclic and Branched Alkane Vapors by Crystal State Pillar[6]arene

Ogoshi, Tomoki; Saito, Kazuki; Sueto, Ryuta; Kojima, Ryosuke; Hamada, Yukie; Akine, Shigehisa; Moeljadi, Adhitya Mangala Putra; Hirao, Hajime; Kakuta, Takahiro; Yamagishi, Toshio

doi:10.1002/anie.201711575

Cited by 111 publications

(110 citation statements)

References 28 publications

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“…Afterward, the separation of branched alkanes from a mixture of linear and branched alkanes using NACs of 30 to improve research octane numbers (RONs) was achieved by Ogoshi et al In addition, we found that NACs of both 29 and 30 can be used to separate cyclic aliphatics from corresponding aromatics . Crystals of 29a separate toluene from methylcyclohexane with a purity of 98.8%, while 30b crystals separate methylcyclohexane from toluene with a purity of 99.2% ( Figure ).…”

Section: Pillararene‐based Comsmentioning

confidence: 85%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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macrocycles. They have been also employed to modify the surface properties of metal nanoparticles via noncovalent host−guest interactions, [31] covering their applications in drug delivery, [32] highly sensitive sensors, [33] selective catalysis, [34] and so on.In addition to their intensive applications based on their host−guest chemistry, macrocycles have also been used as building blocks to construct solid materials including porous organic polymers (POPs), [35,36] metal-organic frameworks (MOFs), [37][38][39][40][41][42][43] and crystalline organic materials (COMs). [44][45][46][47][48][49][50][51][52][53][54][55][56][57] Particular attention should be paid to COMs, a class of organic materials featuring facile preparation, high crystallinity, structural diversity, chemical stability, solution-processability, etc. [58][59][60][61][62][63][64][65][66][67][68][69][70] Different from MOFs that are composed of both inorganic (metal ions) and organic species (organic ligands) through coordination, COMs refer to a kind of crystalline materials composed of pure organics connected by either covalent or noncovalent bonds. [71][72][73] For COMs connected by noncovalent bonds, the typical materials are organic molecular crystals with intriguing properties such as semiconductor, [53] porosity, [68] etc. Owing to the inefficient packing of organic building blocks in the crystal state, some molecular crystals display extrinsic porosity, which are often termed as hydrogen-bonded organic frameworks (HOFs) [74,75] or supramolecular organic frameworks (SOFs). [76][77][78][79][80] For COMs connected by covalent bonds, typical materials are crystalline covalent organic frameworks (COFs), which were firstly reported in 2005 by Yaghi and co-workers [44] Benefitting from rigid chemical bonds and building blocks, COFs show permanent and well-ordered porosity. [45][46][47][48] Supramolecular-macrocycle-based COMs, a class of COMs with macrocycles as the main building blocks, have drawn particular attention in recent years. According to their components, supramolecular-macrocycle-based COMs can be classified into two main categories, the ones composed of pure macrocycles and the others consisting of macrocycles and other simple organic building blocks. Owing to their prefabricated cavities of a certain type, some of macrocycle-based COMs exhibit intrinsic microporosity for guest adsorption in the solid state. On the other hand, the extrinsic porosity of some macrocyclebased COMs may form due to the inefficient packing of these rigid macrocyclic molecules in the crystalline state. In certain circumstances, both intrinsic and extrinsic microporosity can be created in a single lattice of a certain COM, thus leading to Supramolecular macrocycles are well known as guest receptors in supramolecular chemistry, especially host−guest chemistry. In addition to their wide applications in host−guest chemistry and related areas, macrocycles have also been employed to construct crystalline organic materials (COMs) owing to their particular structur...

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Section: Pillararene‐based Comsmentioning

confidence: 85%

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

et al. 2019

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“…We also showed that activated P5A crystals could be used for uptake and sensing of linear alkane vapors,, and separation of linear alkanes with various lengths . In addition, activated pillar[6]arene crystals can be used for isolation of branched alkanes to increase the octane number . However, to our knowledge, this is the first report to show that different molecular arrangements of P5As give rise to different patterns of the uptake, release, and molecular dynamics of the guest in the crystals.…”

Section: Discussionmentioning

confidence: 99%

Host–Guest Complexation Using Pillar[5]arene Crystals: Crystal‐Structure Dependent Uptake, Release, and Molecular Dynamics of an Alkane Guest

Ogoshi

Hamada

Sueto

et al. 2019

Chemistry A European J

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Host–guest complexation has been mainly investigated in solution, and it is unclear how guest molecules access the assembled structures of host and dynamics of guest molecules in the crystal state. In this study, we studied the uptake, release, and molecular dynamics of n‐hexane vapor in the crystal state of pillar[5]arenes bearing different substituents. Pillar[5]arene bearing 10 ethyl groups yielded a crystal structure of herringbone‐type 1:1 complexes with n‐hexane, whereas pillar[5]arene with 10 allyl groups formed 1:1 complexes featuring a one‐dimensional (1D) channel structure. For pillar[5]arene bearing 10 benzyl groups, one molecule of n‐hexane was located in the cavity of pillar[5]arene, and another n‐hexane molecule was located outside of the cavity between two pillar[5]arenes. The substituent‐dependent differences in molecular arrangement influenced the uptake, release, and molecular dynamics of the n‐hexane guest. The substituent effects were not observed in host–guest chemistry in solution, and these features are unique for the crystal state host–guest chemistry of pillar[5]arenes.

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“…In 2018, Ogoshi and coworkers reported a crystal state pillar [6]arene (P6), which they synthesized to separate linear and branched alkanes. [17] Generally, quality of gasoline is evaluated by the research octane numbers (RON). In this work, they demonstrated that isolation of branched alkanes from a mixture of linear and branched alkanes using a vapor sorption material based on pillar [6]arene.…”

Section: Solid Materials Constructed From Pillar[n] Arenesmentioning

confidence: 99%

“…Moreover, according to their adaptive structure, pillar[n]arenes have been used as solid materials recently. [17][18][19] Thus in the third part of this paper, we will review some fascinating cases of selective separation, adsorption purification or sensing materials based on pillar[n] arenes in the solid state. The applications of pillar[n]arenes in advanced materials are not limited in these three fields.…”

Section: Introductionmentioning

confidence: 99%

Advanced Functional Materials Constructed from Pillar[n]arenes

Xiao

Zhong

et al. 2018

Israel Journal of Chemistry

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Pillar[n]arenes are new generation of supramolecular macrocyclic host, which exhibit excellent hostÀguest recognition properties. In the last decade, functional materials constructed from pillar[n]arenes have been attracted more and more attention and displayed outstanding characteristics, such as stimuli-responsiveness, self-healing and adaptability. In this mini-review, we provide a survey of the pillar[n]arene-based literatures covering lightharvesting systems, functional hydrogels, and solid materials. It is anticipated that more and more pillar[n]arenesbased advanced materials with multi-functional properties will appear in the near future.

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Separation of Linear and Branched Alkanes Using Host–Guest Complexation of Cyclic and Branched Alkane Vapors by Crystal State Pillar[6]arene

Cited by 111 publications

References 28 publications

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Supramolecular‐Macrocycle‐Based Crystalline Organic Materials

Host–Guest Complexation Using Pillar[5]arene Crystals: Crystal‐Structure Dependent Uptake, Release, and Molecular Dynamics of an Alkane Guest

Advanced Functional Materials Constructed from Pillar[n]arenes

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