Anti‐kooperative Selbstorganisation mit aufrechterhaltener Emission reguliert durch konformationelle und sterische Effekte

Helmers, Ingo; Hossain, Muhammad Saddam; Bäumer, Nils; Wesarg, Paul; Soberats, Bartolomé; Shimizu, Linda S.; Fernández, Gustavo

doi:10.1002/ange.202200390

Angewandte Chemie

2022

DOI: 10.1002/ange.202200390

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Anti‐kooperative Selbstorganisation mit aufrechterhaltener Emission reguliert durch konformationelle und sterische Effekte

Ingo Helmers

Muhammad Saddam Hossain

Nils Bäumer

et al.

Abstract: In diesem Artikel wird eine Strategie vorgestellt, um das Emissionsverhalten im aggregierten Zustand beizubehalten, indem eine antikooperative Selbstorganisation mit schwachen intermolekularen Farbstoffwechselwirkungen erzwungen wird. Um dieses Ziel zu erreichen, haben wir eine konformationsflexible Monomereinheit 1 mit einem 1,3-substituierten (Diphenyl)harnstoff-Wasserstoffbindungssynthon aufgebaut, das an zwei BODIPY-Farbstoffe mit sterisch anspruchsvollen Trialkoxybenzolsubstituenten in der meso-Position g… Show more

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Cited by 6 publications

References 106 publications

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Host–Guest Complexation‐Induced Aggregation Based on Pyrene‐Modified Cyclodextrins for Improved Electronic Circular Dichroism and Circularly Polarized Luminescence

Liang

et al. 2022

Angewandte Chemie

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Several γ‐cyclodextrin (CD) derivatives mono‐ or di‐substituted by pyrenes at the primary rim of the CD were demonstrated to aggregate into nano‐strips in aqueous solutions, with the pyrene moieties interpenetrating into γ‐CD cavities. The hydrophobic complexation‐induced aggregation provides a rigid chiral environment for the pyrenes and leads to significant electronic circular dichroism (ECD) and circularly polarized luminescence (CPL) activities, giving unprecedently high gabs and glum values up to 4.3×10−2 and 5.3×10−2, respectively. The aggregates lead to excimer emission with high quantum yields and show BCPL and BiCPL up to 338. 6 M−1 cm−1 and 169.3 M−1 cm−1, respectively.

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Host–Guest Complexation‐Induced Aggregation Based on Pyrene‐Modified Cyclodextrins for Improved Electronic Circular Dichroism and Circularly Polarized Luminescence

Liang

et al. 2022

Angewandte Chemie

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Thermoreversible Polymorph Transitions in Supramolecular Polymers of Hydrogen‐Bonded Squaramides

et al. 2022

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Hydrogen‐bonded squaramide (SQ) supramolecular polymers exhibit uncommon thermoreversible polymorph transitions between particle‐ and fiber‐like nanostructures. SQs 1–3, with different steric bulk, self‐assemble in solution into particles (AggI) upon cooling to 298 K, and SQs 1 and 2, with only one dendronic group, show a reversible transformation into fibers (AggII) by further decreasing the temperature to 288 K. Nano‐DSC and UV/Vis studies on SQ 1 reveal a concentration‐dependent transition temperature and ΔH for the AggI‐to‐AggII conversion, while the kinetic studies on SQ 2 indicate the on‐pathway nature of the polymorph transition. Spectroscopic and theoretical studies reveal that these transitions are triggered by the molecular reorganization of the SQ units changing from slipped to head‐to‐tail hydrogen bonding patterns. This work unveils the thermodynamic and kinetic aspects of reversible polymorph transitions that are of interest to develop stimuli‐responsive systems.

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Anticooperative Supramolecular Oligomerization Mediated by V‐Shaped Monomer Design and Unconventional Hydrogen Bonds

et al. 2023

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After more than three decades of extensive investigations on supramolecular polymers, strategies for self‐limiting growth still remain challenging. Herein, we exploit a new V‐shaped monomer design to achieve anticooperatively formed oligomers with superior robustness and high luminescence. In toluene, the monomer‐oligomer equilibrium is shifted to the monomer side, enabling the elucidation of the molecular packing modes and the resulting (weak) anticooperativity. Steric effects associated with an antiparallel staircase organization of the dyes are proposed to outcompete aromatic and unconventional B−F⋅⋅⋅H−N/C interactions, restricting the growth at the stage of oligomers. In methylcyclohexane (MCH), the packing modes and the anticooperativity are preserved; however, pronounced solvophobic and chain‐enwrapping effects lead to thermally ultrastable oligomers. Our results shed light on understanding anticooperative effects and restricted growth in self‐assembly.

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Anti‐kooperative Selbstorganisation mit aufrechterhaltener Emission reguliert durch konformationelle und sterische Effekte

Cited by 6 publications

References 106 publications

Host–Guest Complexation‐Induced Aggregation Based on Pyrene‐Modified Cyclodextrins for Improved Electronic Circular Dichroism and Circularly Polarized Luminescence

Host–Guest Complexation‐Induced Aggregation Based on Pyrene‐Modified Cyclodextrins for Improved Electronic Circular Dichroism and Circularly Polarized Luminescence

Thermoreversible Polymorph Transitions in Supramolecular Polymers of Hydrogen‐Bonded Squaramides

Anticooperative Supramolecular Oligomerization Mediated by V‐Shaped Monomer Design and Unconventional Hydrogen Bonds

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