Host–guest chemistry of giant molecular shape amphiphiles based on POSS–PDI conjugates

Chen, Jia; Lin, Heng-Yi; Ji, Xiaohuan; Zhao, Haoru; Sun, Bin; Wang, Chien‐Lung; Zhu, Meifang

doi:10.1039/d0nr08934f

Cited by 7 publications

(6 citation statements)

References 37 publications

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“…33 We obtained the targeted inorganic-organic hybrid TOC–PDI–POSS via imide formation between NH 2 –TOC and PDI–POSS, which has been widely applied to the perylene bisimide-based rigid giant tetrahedra and other perylene bisimide-based organic molecules. 34 As shown in Fig. S3,† the 1 H-NMR spectrum of TOC–PDI–POSS exhibits a unique peak of PDI–POSS, which indicates that PDI–POSS can successfully anchor on the TOC.…”

Section: Resultsmentioning

confidence: 91%

S-scheme enhanced photocatalysis on titanium oxide clusters functionalized with soluble perylene diimides

Dai

Zhang

et al. 2022

J. Mater. Chem. A

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Section: Resultsmentioning

confidence: 91%

S-scheme enhanced photocatalysis on titanium oxide clusters functionalized with soluble perylene diimides

Dai

Zhang

et al. 2022

J. Mater. Chem. A

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“…The aromatic PDI derivatives tend to associate into extended stacks via strong π–π interactions, but the steric repulsion between the POSS groups limits this extension and only dimers of POSS-PDI-POSS are formed in solid state. Pyrene or perylene can be accommodated within the solid assemblies as guest molecules via charge transfer interactions, suggesting there are cavities formed . These cavities may be able to hold water in an aqueous self-assembly to create colloidal stability, although the molecules are hydrophobic without water-soluble groups.…”

Section: Introductionmentioning

confidence: 99%

“…Pyrene or perylene can be accommodated within the solid assemblies as guest molecules via charge transfer interactions, suggesting there are cavities formed. 28 These cavities may be able to hold water in an aqueous self-assembly to create colloidal stability, although the molecules are hydrophobic without water-soluble groups.…”

Section: ■ Introductionmentioning

confidence: 99%

Aqueous Self-Assembly of Hydrophobic Molecules Influenced by the Molecular Geometry

Chen

Zheng

et al. 2022

J. Phys. Chem. B

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Water, in addition to acting as a solvent, plays a constructional role in aqueous self-assembly. The hydrophobic molecule of POSS-PDI-POSS (POSS = polyhedral oligomeric silsesquioxanes, PDI = perylene diimide) has a shape anisotropy in which POSS is a ball-like bulky group and PDI is a flat aromatic group. The self-assembly of this molecule in water created assemblies with inner spaces due to the steric effect, which suppressed aromatic interactions of PDI and trapped water for the colloidal stability. By replacing POSS with dodecyl (C12), C12-PDI-C12 aggregated with extended aromatic interaction of PDI and less inner water. The resulting aggregates tended to agglomerate and precipitate. This discovery extended the scope of aqueous self-assembly by using the building blocks without amphiphilicity and created knowledge for biophysics.

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“…It is a unimolecular quaternary clip ( Q-clip ) that owns eight N -hexyl-1,4,6,8-naphthalene diimide ( NDI ) as the capture units. Meanwhile, pyrene serves as a guest molecule and a nanotemplating reagent to facilitate the charge transfer (CT) interactions and coassemble with the Q-clip . − The types of noncovalent interactions in the Q-clip:pyrene mixtures can be adjusted by the composition of the mixture. As shown in Figure a,b, both the NDI-NDI π-π interaction and NDI-pyrene CT interaction are present in the 1:4 Q-clip:pyrene mixture (denoted as Q-clip:pyrene 4 ), whereas there is only NDI-pyrene CT interaction in the1:8 Q-clip:pyrene mixture (denoted as Q-clip:pyrene 8 ).…”

Section: Introductionmentioning

confidence: 99%

Composition-Driven Structural Modulation and Guest-Induced Nanotemplate Effects of the Host–Guest Complexes Made by a Unimolecular Q-Clip

Yang

Lin

et al. 2021

Macromolecules

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The composition of a self-assembly system has long been an essential factor that governs the resulting supramolecular structures. Nevertheless, due to the rigorous demands of structural compatibility in host–guest chemistry, the molar ratio of host–guest mixtures has not been applied as a significant factor in modulating the supramolecular structures of host–guest complexes. In this study, via using a novel unimolecular quaternary clip (Q-clip) as the host molecule and pyrene as the guest molecule and a nanotemplating reagent, we discovered that the changes in the molar ratios of the Q-clip:pyrene mixtures resulted in the structural modulation of the host–guest complexes. Supramolecular lamellae made by the 1:4 Q-clip:pyrene mixture and a hexagonal columnar phase (Colh) made by the 1:8 Q-clip:pyrene mixture were identified by the 1D powder and 2D fiber WAXS characterizations. Time-resolved synchrotron X-ray characterization and thermal analysis further showed that removing the easily sublimed guest molecules (pyrene) via thermal annealing simply hollowed out the supramolecular structures without damaging the supramolecular scaffolds made by the Q-clips. Pyrene is thus a nanotemplating reagent that can be used to create the hollowed-out 2D lamellar and 1D cylindrical scaffolds of Q-clips. The study thus gave a novel example of a host–guest mixture that is able to carry out composition-driven structural modulation and guest-induced nanotemplates. The finding broadens the horizon of host–guest chemistry and may inspire more nanoinnovation.

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Host–guest chemistry of giant molecular shape amphiphiles based on POSS–PDI conjugates

Abstract: Giant shape amphiphiles (GSA) are giant molecules made with nano-building blocks that have distinct shapes. The incompatible packing behaviors of the nano-building blocks of GSA could create cavities within certain...

Cited by 7 publications

References 37 publications

S-scheme enhanced photocatalysis on titanium oxide clusters functionalized with soluble perylene diimides

S-scheme enhanced photocatalysis on titanium oxide clusters functionalized with soluble perylene diimides

Aqueous Self-Assembly of Hydrophobic Molecules Influenced by the Molecular Geometry

Composition-Driven Structural Modulation and Guest-Induced Nanotemplate Effects of the Host–Guest Complexes Made by a Unimolecular Q-Clip

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