Supramolecular polymerization of hydrogen-bonded rosettes with anthracene chromophores: regioisomeric effect on nanostructures

Prabhu, Deepak D.; Aratsu, Keisuke; Yamauchi, Mitsuaki; Xu, Lin; Adhikari, Bimalendu; Yagai, Shiki

doi:10.1038/pj.2016.94

Cited by 4 publications

(1 citation statement)

References 55 publications

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“…Seminal work by Yagai et al has shown the barbiturate unit can be employed to guide the assembly of various nanostructures such as rods, rings, coils, and catenanes. [42][43][44][45] In addition, the HB-induced arrangement of a monotopic π-conjugated system featuring a barbiturate unit was studied by STM. 46 Similar to previous work done on DAT derivatives, barbiturate systems have also been demonstrated to form HB-induced hexameric rosettes at the solid-liquid interface.…”

Section: Introductionmentioning

confidence: 99%

Structure–Assembly–Property Relationships of Simple Ditopic Hydrogen-Bonding-Capable π-Conjugated Oligomers

Weldeab

Kornman

et al. 2021

Organic Materials

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A series of simple ditopic hydrogen bonding capable molecules functionalized with 2,4-diamino-1,3,5-triazine (DAT), barbiturate (B), and phthalhydrazide (PH) on both termini of a 2,2′-bithiophene linker were designed and synthesized. The intrinsic electronic structures of the ditopic DAT, PH, and B molecules were investigated with ground-state DFT calculations. Their solution absorbance was investigated with UV-vis, where it was found that increasing size of R group substituent on the bithiophene linker resulted in a general blue-shift in solution absorbance maximum. The solid-state optical properties of ditopic DAT and B thin films were evaluated by UV-vis, and it was found that the solid-state absorbance was red-shifted with respect to solution absorbance in all cases. The three DAT molecules were vacuum thermal deposited onto Au(111) substrates and the morphologies were examined using STM. (DAT-T)2 was observed to organize into six-membered rosettes on the surface, whereas (DAT-TMe)2 formed linear assemblies before and after thermal annealing. For (DAT-Toct)2 , an irregular arrangement was observed, while (B-TMe)2 showed several co-existent assembly patterns. The work presented here provides fundamental molecular-supramolecular relationships useful for semiconductive materials design based on ditopic hydrogen bonding capable building blocks.

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Section: Introductionmentioning

confidence: 99%

Structure–Assembly–Property Relationships of Simple Ditopic Hydrogen-Bonding-Capable π-Conjugated Oligomers

Weldeab

Kornman

et al. 2021

Organic Materials

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Self‐Assembly of 9,10‐Bis(phenylethynyl) Anthracene (BPEA) Derivatives: Influence of π–π and Hydrogen‐Bonding Interactions on Aggregate Morphology and Self‐Assembly Mechanism

Lübtow

Helmers

Stepanenko

et al. 2017

Chemistry A European J

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9,10-Bis(phenylethynyl)anthracenes (BPEAs) are an important class of dyes in various applications including chemiluminescence emitters, materials for photon upconversion, and for optoelectronic devices. Some of these applications require control over the packing modes of the molecules within the active layer, which can be effected by bottom-up self-assembly. Studies aimed at controlling the molecular organization of BPEAs have primarily focused on bulk or liquid-crystal materials, whereas in-depth investigations of BPEA-based assemblies in solution remain elusive. In this article, the self-assembly of two new BPEA derivatives with hydrophobic side chains is reported, one of them featuring amide functional groups and the other one lacking them. Comparison of the self-assembly behavior of both systems in solution using spectroscopic (UV/Vis, fluorescence, and NMR), microscopic (AFM), and theoretical (PM6) studies reveals the crucial role of the amide groups in controlling the self-assembly. For both systems, the formation of H-type face-to-face π-stacks is proposed, whereas the interplay of π-stacking and H-bonding is responsible for driving the formation of 1D stacks and increasing the binding constant by two to three orders of magnitude. Our findings show that H-bonding is a prerequisite to create ordered BPEA assemblies in solution.

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Unravelling denaturation, temperature and cosolvent-driven chiroptical switching in peptide self-assembly with switchable piezoelectric responses

Ramesh,

Das,

Maji

et al. 2024

Chem. Sci.

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Supramolecular polymerization of hydrogen-bonded rosettes with anthracene chromophores: regioisomeric effect on nanostructures

Cited by 4 publications

References 55 publications

Structure–Assembly–Property Relationships of Simple Ditopic Hydrogen-Bonding-Capable π-Conjugated Oligomers

Structure–Assembly–Property Relationships of Simple Ditopic Hydrogen-Bonding-Capable π-Conjugated Oligomers

Self‐Assembly of 9,10‐Bis(phenylethynyl) Anthracene (BPEA) Derivatives: Influence of π–π and Hydrogen‐Bonding Interactions on Aggregate Morphology and Self‐Assembly Mechanism

Unravelling denaturation, temperature and cosolvent-driven chiroptical switching in peptide self-assembly with switchable piezoelectric responses

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