Docking Strategy To Construct Thermostable, Single‐Crystalline, Hydrogen‐Bonded Organic Framework with High Surface Area

Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo; Cohen, Boiko; Tohnai, Norimitsu; Douhal, Abderrazzak

doi:10.1002/anie.201805472

Cited by 112 publications

(76 citation statements)

References 63 publications

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“…[23] Te ctons 4 and 5 form stable HOFs (HOF-TCBP [24] and PFC-1, [9] respectively), which have al arge surface area with SA (BET) values of 2066 and 2122 m 2 g À1 ,r espectively.C ao and co-workers demonstrated that photoactive PFC-1 could encapsulate Doxorubicin, allowing synergetic chemo-photodynamic therapy. [9] Hisaki, Douhal, and co-workers proposed that shape-fitted docking of twisted hexaazatriphenylene (HAT) derivatives 6a,b,c provided robust HOFs with permanent porosity,a nd constructed as eries of HAT-based HOFs CPHAT-1, [25] CBPHAT-1, [26] and CTolHAT-1. [27] Activated CPHAT-1a had an SA (BET) value of 649 m 2 g À1 and was thermally stable up to 339 8 8C.…”

Section: Carboxylic Acidmentioning

confidence: 99%

“…[25] Similarly,activated CBPHAT-1a had an SA (BET) value of 1288 m 2 g À1 and was stable up to 305 8 8C. [26] Tr iptycene derivative 7 remarkably yielded two types of interpenetration isomeric PHTHOF-1 and PHTHOF-2,w ith different numbers of interpenetrated acs-networks.T heir SA (BET) values were 1140 m 2 g À1 and 1690 m 2 g À1 ,r espectively. [28] The JLU-SOF-1-R composed of the homochiral tecton 8 had an SA (BET) value of 460 m 2 g À1 and selective sorption toward CO 2 .…”

Section: Carboxylic Acidmentioning

confidence: 99%

“…[20,[30][31][32] Interestingly,tripyrazole derivatives 27-29 (Figure 7 (Figure 9d). [25][26][27] Tr iptycene derivatives 16 and 17 produced isostructural HOFs, [39] and compound 17 was expected to possess an extremely large surface area with an SA (BET) value of 3599 m 2 g À1 .…”

Section: Isostructural Frameworkmentioning

confidence: 99%

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Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity

et al. 2019

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Designing organic components that can be used to construct porous materials enables the preparation of tailored functionalized materials. Research into porous materials has seen a resurgence in the past decade as a result of finding of self‐standing porous molecular crystals (PMCs). Particularly, a number of crystalline systems with permanent porosity that are formed by self‐assembly through hydrogen bonding (H‐bonding) have been developed. Such systems are called hydrogen‐bonded organic frameworks (HOFs). Herein we systematically describe H‐bonding patterns (supramolecular synthons) and molecular structures (tectons) that have been used to achieve thermal and chemical durability, a large surface area, and functions, such as selective gas sorption and separation, which can provide design principles for constructing HOFs with permanent porosity.

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Section: Carboxylic Acidmentioning

confidence: 99%

Section: Carboxylic Acidmentioning

confidence: 99%

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Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity

et al. 2019

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“…Hydrogen-bonded organic frameworks (HOFs) are a class of newly emerged crystalline porous materials (CPMs) (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). In contrast to classic CPMs such as inorganic zeolites (21), metal-organic frameworks (MOFs) (22), and covalent organic frameworks (COFs) (23), HOFs are obviously out of the ordinary, as they are classic supramolecular compounds, where hydrogen bonds contribute to their framework stability, as can be derived from the term itself.…”

Section: Introductionmentioning

confidence: 99%

π-π stacking interactions: Non-negligible forces for stabilizing porous supramolecular frameworks

et al. 2020

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Revealing the contribution of - stacking interactions in supramolecular assembly is important for understanding the intrinsic nature of molecular assembly fundamentally. However, because they are much weaker than covalent bonds, - stacking interactions are usually ignored in the construction of porous materials. Obtaining stable porous materials that are only dependent on - stacking interactions, despite being very challenging, could address this concern. Here, we present a porous supramolecular framework (-1) stabilized only by intermolecular - stacking interactions. -1 shows good thermal and chemical stability not only in various organic solvents but also in aqueous solution in a broad pH range. Furthermore, featuring one-dimensional channels with dangling thiolate groups, -1 exhibits excellent Hg 2+ removal performance, with adsorption capacity as high as 786.67 mg g −1 and an adsorption ratio as high as 99.998%. In addition, -1 also shows high adsorption selectivity to Hg 2+ in the presence of a series of interfering ions.

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“…Hydrogen bonds often play very important roles in the structures and physical properties of a variety of materials in biological chemistry and organic, inorganic, and organic–inorganic hybrid chemistry. And a variety of hydrogen bond‐supported molecular assemblies have been synthesized to find new hydrogen‐bonding patterns, for example, hydrogen‐bonded organic frameworks (HOFs), hydrogen‐bonded host frameworks (HHFs), which showed porous, ferroelectric, energetic, and other physical properties . Herein we demonstrated the first example of hydrogen‐bonding docking strategy for reversible specific sensing trifluoroacetic acid (TFA) vapor based on pure organic crystals (Figure b).…”

Section: Introductionmentioning

confidence: 99%

Reversible Specific Vapoluminescence Behavior in Pure Organic Crystals through Hydrogen‐Bonding Docking Strategy

Xia

Jiang

Shen

et al. 2019

Advanced Optical Materials

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interactions (e. g., weak M-M interactions, metallophilic interactions, π-stacking, and coordination modes) in transition-metal assemblies can easily be perturbed with uptaking certain vapors into the crystal lattice, thereby inducing dramatic changes in emission color. [10][11][12][13][14][15][16][17][18] Moreover, relevant researches evidenced that isomer conversion of metal-complexes with remarkable emission color change can also be controlled through exposure to different vapor, which rendered a new approach to access great vapoluminescent materials. [19][20][21][22] Still and all, the metal-containing vapoluminescent compounds are generally expensive, difficult to synthesis, and environmentally unfriendly, thus limits their practical application.An alternative strategy is to construct pure organic vapoluminescent crystals by rational design, in viewing of their low cost, hypotoxicity, and molecular diversity. [23][24][25][26][27][28] Furthermore, the well-known aggregation-induced emission (AIE) [29][30][31] and crystallization-induced emission enhancement (CIEE) [32] phenomenon largely increases the possibility of exploring organic vapoluminescence materials with high solid-state emission efficiency. To date, a variety of organic compounds incorporated 1,8-naphthalimides (NPIs), [33,34] tetraphenylethene (TPE), [35][36][37] and squaraine [38][39][40] have been well studied as vapoluminescent materials. In those materials, luminescent changes are generally depending on molecular sliding resulted from the cavities in crystalline lattices undiscerningly inserted by vapor molecules with suitable shape and size, thereby leads to a nonspecific detection (Figure 1a). And also, there are very few examples of reversible luminescence change in organic crystal due to pseudopolymorphic transformations, such as solvation/desolvation and solvent exchange processes. Besides, some emissive porous organic frameworks have also emerged as vapoluminescence materials in viewing of their excellent gas adsorption property, but the results turned out to be unsatisfied. [41][42][43][44][45][46] As such, a novel design strategy for reversibly detecting specific vapor molecule in organic vapoluminescent materials is urgent desired and would prove beneficial to not only sensing, but also recording and biological applications. The design of vapoluminescence materials with high contrast, selectivity, and reversibility toward certain vapors is extremely attractive but remains a long-standing challenge. In this work, crystallization of squaraine dye (SQ) molecules in different solvents affords two organic crystals (R-SQ andSQ-2TFA) with the fluorescence quantum yield up to 0.81, which shows reversible phase transition of the crystals with different emission color via annealing treatment and solvent-vapor adsorption. From spectral and powder X-ray diffraction analysis, exposure of green-emitting R-SQ crystals to trifluoroacetic acid (TFA) vapor gives cyan-emitting SQ-2TFA crystals, while desorption of SQ-2TFA crystals by heating recovers R...

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Docking Strategy To Construct Thermostable, Single‐Crystalline, Hydrogen‐Bonded Organic Framework with High Surface Area

Cited by 112 publications

References 63 publications

Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity

Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity

π-π stacking interactions: Non-negligible forces for stabilizing porous supramolecular frameworks

Reversible Specific Vapoluminescence Behavior in Pure Organic Crystals through Hydrogen‐Bonding Docking Strategy

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