Stable Heterotopic Noncovalent Resorcin[4]arene Assemblies

Higler, Irene; Grave, Lennart; Breuning, Esther; Verboom, Willem; Jong, Feike de; Fyles, Thomas M.; Reinhoudt, David N.

doi:10.1002/(sici)1099-0690(200005)2000:9<1727::aid-ejoc1727>3.3.co;2-s

Cited by 9 publications

(19 citation statements)

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“…Because of the absence of reasonable multicomponent self-assembly systems that provide both cyclic and polymeric hydrogen-bonded aggregates soluble without forming higher-order assemblies, the structural preference for these competing hydrogen-bonded motifs have been mainly studied based on solid-state packing structures provided by X-ray crystallography 29 or theoretical approaches 30 . Following vapor pressure osmometry (VPO) 31 32 33 and nuclear magnetic resonance (NMR) studies of 1 and 2 in chloroform however reveal such a structural preference could occur in equilibrated solution state.…”

Section: Resultsmentioning

confidence: 99%

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High-fidelity self-assembly pathways for hydrogen-bonding molecular semiconductors

Suzuki

Gushiken

et al. 2017

Sci Rep

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The design of molecular systems with high-fidelity self-assembly pathways that include several levels of hierarchy is of primary importance for the understanding of structure-function relationships, as well as for controlling the functionality of organic materials. Reported herein is a high-fidelity self-assembly system that comprises two hydrogen-bonding molecular semiconductors with regioisomerically attached short alkyl chains. Despite the availability of both discrete cyclic and polymeric linear hydrogen-bonding motifs, the two regioisomers select one of the two motifs in homogeneous solution as well as at the 2D-confined liquid-solid interface. This selectivity arises from the high directionality of the involved hydrogen-bonding interactions, which renders rerouting to other self-assembly pathways difficult. In thin films and in the bulk, the resulting hydrogen-bonded assemblies further organize into the expected columnar and lamellar higher-order architectures via solution processing. The contrasting organized structures of these regioisomers are reflected in their notably different miscibility with soluble fullerene derivatives in the solid state. Thus, electron donor-acceptor blend films deliver a distinctly different photovoltaic performance, despite their virtually identical intrinsic optoelectronic properties. Currently, we attribute this high-fidelity control via self-assembly pathways to the molecular design of these supramolecular semiconductors, which lacks structure-determining long aliphatic chains.

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Section: Resultsmentioning

confidence: 99%

“…Furthermore, the presence of residual monomers (ca. 20%) in the monomer-aggregate equilibrium could seriously influence c collig , leading to this underestimation of N 32 . On the contrary, 2 exhibited a linear increase of N with increasing concentration, and N reached 9.9 for c = 100 mM.…”

Section: Resultsmentioning

confidence: 99%

High-fidelity self-assembly pathways for hydrogen-bonding molecular semiconductors

Suzuki

Gushiken

et al. 2017

Sci Rep

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“…Apart from conventional characterisation techniques ( 1 H NMR, ESI‐MS, UV/Vis, and elemental analysis), vapour pressure osmometry (VPO) was applied to characterise R3 as one of the aggregates. VPO is a very useful method to analyse self assembled systems even if they are dynamic;15 unfortunately, this technique has not been utilised frequently. For R3 VPO provided a molar mass of 2417 Da, which is in excellent agreement (–2 %) with the mass obtained from ESI‐MS (2473).…”

Section: Approach IImentioning

confidence: 99%

Supramolecular Copper Phenanthroline Racks: Structures, Mechanistic Insight and Dynamic Nature

et al. 2005

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Herein, we describe the preparation of several dynamic multicomponent supramolecular racks based on copper phenanthroline complexes using the HETPHEN concept (heteroleptic bisphenanthroline complexes). This approach employs bulky aryl substituents at the bisimine coordination sites to control the coordination equilibrium. The racks were characterised by spectroscopic methods, both in solution (1H NMR, ESI‐MS, UV/Vis, vapour pressure osmometry) and in the solid state (X‐ray). Ligand exchange studies established the reversible nature of the aggregates, the details of which are vital for the development of higher level multicomponent structures. In this regard, the present rack assemblies contrast to the large multitude of known rack motifs that are almost exclusively built using kinetically inert coordination building blocks. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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“…[238,239] Die beiden Resorcareneinheiten in diesem Komplex werden durch vier geladene H-Brücken zusammengehalten, die sich zwischen den anionischen Phenolat-und den Phenolgruppen bilden. [241] Calix [4]arene gehören zur gleichen Verbindungsklasse wie Resorcarene und Cavitanden. [240] Reinhoudt und Mitarbeiter beschrieben die Heterodimerisierung zweier Cavitanden über vierfache Pyridin-Carbonsäure-Wechselwirkungen mit einer Assoziationskonstanten von über 10 7 m À1 in Chloroform.…”

Section: Strukturelles Design H-verbrückter Kapselnunclassified