4.8 Review

Chirality of Perylene Diimides: Design Strategies and Applications

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π-Scaffold

Ben Teichmann et al.

Summary: This study introduces the concept of tailored chiral pi-surfaces and demonstrates enantioselective binding through pure van-der-Waals interactions. The BPTI receptor with a contorted pi-scaffold achieved significant enantiodifferentiation with (P)- and (M)-[6]helicene. The enantioselective recognition is observable by the naked eye.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Chemistry, Multidisciplinary

Design and Control of Perylene Supramolecular Polymers through Imide Substitutions

Robert S. Wilson-Kovacs et al.

Summary: This paper provides a critical overview of the challenges faced by new supramolecular polymer systems and discusses approaches related to controlling perylene-based SMPs through chemical modification of imide substituents. The authors highlight recent methods to control morphology, aggregation, and growth mechanism of SMPs using thermodynamic and kinetic control, emphasizing the importance of these functional SMPs for potential future exploration and application.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Article Chemistry, Multidisciplinary

High-Performance Organic Electronic Materials by Contorting Perylene Diimides

Cedric Schaack et al.

Summary: This perspective discusses the higher performance of organic electronic devices achieved by contorting PDI, how different modes of contortion can modify the observed optical and electronic properties of PDI, and the opportunities for continued study in this rapidly developing organic materials frontier.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Chemistry, Multidisciplinary

Inducing Single-Handed Helicity in a Twisted Molecular Nanoribbon

Rajeev K. Dubey et al.

Summary: Molecular conformation plays a crucial role in chemistry and materials science. The synthesis of single-handed helically twisted molecular nanoribbons remains a challenge, but an asymmetric approach has been described to induce single-handed helicity with excellent conformational discrimination.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Review Chemistry, Multidisciplinary

Supramolecularly Engineered J-Aggregates Based on Perylene Bisimide Dyes

Markus Hecht et al.

Summary: The discovery of the self-assembly of cyanine dyes into J-aggregates had a significant impact on dye chemistry, leading to the emergence of new useful properties. Despite a good theoretical understanding of their structure-property relationships, examples of J-aggregates remained scarce due to the lack of supramolecular designs to guide their formation. The use of nature's supramolecular blueprint in the development of J-aggregates of perylene bisimides (PBIs) has shown promise in various applications, such as high-performance color pigments and organic semiconductors.

ACCOUNTS OF CHEMICAL RESEARCH (2021)

Review Chemistry, Multidisciplinary

Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes

Tadashi Mori

Summary: This review focuses on the chiroptical properties of multiple helicenes, with an emphasis on the impact of the arrangement of multiple helices on the chiroptical responses. Although the number of multiple helicenes reported is limited, insights into the design principle for advanced chiroptical materials through the proper arrangement of multiple helices are provided.

CHEMICAL REVIEWS (2021)

Article Chemistry, Physical

Origin of Chiroptic Amplification in Perylene-Diimide Helicenes

Daniel Aranda et al.

Summary: It has been shown that NP3H exhibits an enhancement of the electronic circular dichroism response in the visible range, attributed to the increase in the magnetic transition dipole moments of the involved electronic states, mainly due to the presence of the double [6]helicene substructure within NP3H. This phenomenon is suggested to arise from an exciton-like coupling, not present in the analogue NPDH. Further computations and analysis support this mechanism, indicating the potential for the double [6]helicene unit to be a key core in designing new chiral conjugated materials with enhanced chiroptical properties in the visible range.

JOURNAL OF PHYSICAL CHEMISTRY C (2021)

Article Chemistry, Multidisciplinary

Chirality Amplified: Long, Discrete Helicene Nanoribbons

Xiao Xiao et al.

Summary: In this study, two polyhelicene frameworks were synthesized, with 18 and 24 fused benzene rings, respectively, exhibiting the largest electronic circular dichroism in the visible spectrum. These helical nanoribbons incorporate multiple helicenes, showing interesting chemical, biological, and chiroptical properties. Coupling with perylene-diimide subunits enhances chiroptic response, with the possibility of further enhancement by axial elongation.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Multidisciplinary Sciences

π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

Li Zhang et al.

Summary: In this study, a novel approach of skeleton merging was introduced to address the dilemma between strong coupling with circular polarized light and high charge-carrier mobility in high-performance chiral organic semiconducting molecules. The resulting pi-extended double helicene structure exhibits high dissymmetry factor, extended pi-planar system for charge transport properties, near-infrared light absorption, and ambipolar charge transport abilities, enabling high photoresponsivity and external quantum efficiency in both p- and n-type modes under NIR light irradiation. These characteristics allow for high-performance broadband CPL detections up to the NIR spectral region.

NATURE COMMUNICATIONS (2021)

Article Chemistry, Multidisciplinary

Supramolecular Chirality Transfer toward Chiral Aggregation: Asymmetric Hierarchical Self-Assembly

Shuai Huang et al.

Summary: This paper summarizes recent studies on chirality transfer induced self-assembly based on various supramolecular interactions, and discusses the impact of different environments and system states on the expression of chirality, as well as the driving forces that facilitate chiral bias and the role of supramolecular interactions.

ADVANCED SCIENCE (2021)

Article Chemistry, Multidisciplinary

Deracemization of Carbohelicenes by a Chiral Perylene Bisimide Cyclophane Template Catalyst

Manuel Weh et al.

Summary: The deracemization process of a racemic mixture of chiral molecules into enantioenriched compounds is achieved by an inherently chiral perylene bisimide cyclophane, which can transform [5]-helicene into an enantioenriched mixture with a high enantiomeric excess. The macrocyclic supramolecular host shows strong and enantioselective binding towards homochiral carbohelicenes, suggesting potential applications in template-catalyzed deracemization processes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

Perspectives in Dye Chemistry: A Rational Approach toward Functional Materials by Understanding the Aggregate State

David Bialas et al.

Summary: The past 20 years have seen a renaissance in dye chemistry, transitioning from traditional colorant research to functional materials. Functional material properties are governed by intermolecular interactions, rather than molecular structure alone. Future research should focus on developing larger oligomers and being guided by theoretical predictions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area

Rebecca Renner et al.

Summary: A series of Perylene Bisimide (PBI) dyes with various aryl substituents in 1,6,7,12 bay positions have been synthesized through Suzuki cross-coupling reaction. These molecules exhibit a large and fixed twist angle of the PBI pi-core due to high steric congestion, leading to substantial racemization barriers and the potential for isolation of enantiopure atropoisomers. Variable temperature NMR studies reveal a multitude of conformational isomers in solution, interconverted via smaller activation barriers, while their redox and optical properties have been characterized through various spectroscopic techniques.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Article Chemistry, Multidisciplinary

Chiral Supramolecular Polymers Assembled by Amphiphilic Oligopeptide-Perylene Diimides and High Electrochemical Sensing

Duo Wei et al.

Summary: This study utilizes synthesized oligopeptide-perylene diimides (AUPDIs) to generate beta-sheet strands, forming a diversity of morphologies in supramolecular polymers in aqueous media. Complex morphology transitions can be controlled by adjusting the water volume fraction, leading to efficient electronic sensing capabilities.

LANGMUIR (2021)

Review Chemistry, Multidisciplinary

Dually cross-linked single networks: structures and applications

Maksim Rodin et al.

Summary: Supramolecular chemistry offers dynamic interactions for polymeric gels, providing reversibility and responsiveness to external stimuli, addressing the limitations of traditional cross-linked polymers. By combining different types of cross-links in a single gel, researchers have created versatile materials with improved mechanical performance and multifunctionality for applications in various fields.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Multidisciplinary

Chiral Supraparticles for Controllable Nanomedicine

Jihyeon Yeom et al.

ADVANCED MATERIALS (2020)

Article Chemistry, Multidisciplinary

A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics

Zetong Ma et al.

SCIENCE CHINA-CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

Artificial Chiral Probes and Bioapplications

Changlong Hao et al.

ADVANCED MATERIALS (2020)

Review Chemistry, Multidisciplinary

Supramolecular Chiral Nanoarchitectonics

Katsuhiko Ariga et al.

ADVANCED MATERIALS (2020)

Article Chemistry, Multidisciplinary

Enzyme-Triggered Disassembly of Perylene Monoimide-based Nanoclusters for Activatable and Deep Photodynamic Therapy

Yang Cai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Perylene Diimide-Embedded Double [8]Helicenes

Bo Liu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Self-Sorting Supramolecular Polymerization: Helical and Lamellar Aggregates of Tetra-Bay-Acyloxy Perylene Bisimide

Markus Hecht et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Surface-Doped Quasi-2D Chiral Organic Single Crystals for Chiroptical Sensing

Xiaobo Shang et al.

ACS NANO (2020)

Article Chemistry, Multidisciplinary

Supramolecular Chiral Aggregates Exhibiting Nonlinear CD-ee Dependence

Xiaosheng Yan et al.

ADVANCED MATERIALS (2020)

Review Chemistry, Multidisciplinary

Chiroptical Properties in Thin Films of π-Conjugated Systems

Gianluigi Albano et al.

CHEMICAL REVIEWS (2020)

Review Nanoscience & Nanotechnology

Functional organic dyes for health-related applications

Wenyu Cheng et al.

Article Multidisciplinary Sciences

Control of self-assembly pathways toward conglomerate and racemic supramolecular polymers

Marius Wehner et al.

NATURE COMMUNICATIONS (2020)

Review Chemistry, Multidisciplinary

Stereospecific interactions between chiral inorganic nanomaterials and biological systems

Xueli Zhao et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Corannurylene Pentapetalae

Dong Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Cell Biology

The Origin of Biological Homochirality

Donna G. Blackmond

COLD SPRING HARBOR PERSPECTIVES IN BIOLOGY (2019)

Review Chemistry, Multidisciplinary

Semiconducting Perylene Diimide Nanostructure: Multifunctional Phototheranostic Nanoplatform

Zhen Yang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Review Chemistry, Multidisciplinary

Noncovalent Aqua Materials Based on Perylene Diimides

Elisha Krieg et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Review Chemistry, Multidisciplinary

From Dyestuff Chemistry to Cancer Theranostics: The Rise of Rylenecarboximides

Chendong Ji et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

Article Chemistry, Multidisciplinary

Aromatic-Diimide-Based n-Type Conjugated Polymers for All-Polymer Solar Cell Applications

Jing Yang et al.

ADVANCED MATERIALS (2019)

Article Chemistry, Multidisciplinary

A Water-Soluble, NIR-Absorbing Quaterrylenediimide Chromophore for Photoacoustic Imaging and Efficient Photothermal Cancer Therapy

Chang Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Nanographene Imides Featuring Dual-Core Sixfold [5]Helicenes

Guogang Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Organic

Progress in the synthesis of perylene bisimide dyes

Agnieszka Nowak-Krol et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

Article Chemistry, Multidisciplinary

Co(II) Induced Aggregation of Chiral Perylene Derivatives and Macroscopic Formation of Supramolecular Networks

Pradip Kumar Sukul et al.

CHEMISTRY LETTERS (2018)

Article Chemistry, Multidisciplinary

A Helicene Nanoribbon with Greatly Amplified Chirality

Nathaniel J. Schuster et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

A Crystalline π-Stack Containing Five Stereoisomers: Insights into Conformational Isomorphism, Chirality Inversion, and Disorder

Agnieszka Nowak-Krol et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Analyzing Spin Selectivity in DNA-Mediated Charge Transfer via Fluorescence Microscopy

John M. Abendroth et al.

ACS NANO (2017)

Article Chemistry, Physical

Dual-Stimulus-Responsive Fluorescent Supramolecular Prodrug for Antitumor Drug Delivery

Wenyu Cheng et al.

CHEMISTRY OF MATERIALS (2017)

Review Chemistry, Multidisciplinary

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

Frank Wuerthner et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Multidisciplinary

A supramolecular helix that disregards chirality

Cecile Roche et al.

NATURE CHEMISTRY (2016)

Review Chemistry, Multidisciplinary

Water-soluble perylenediimides: design concepts and biological applications

Mengmeng Sun et al.

CHEMICAL SOCIETY REVIEWS (2016)

Article Chemistry, Multidisciplinary

Self-Discriminating Termination of Chiral Supramolecular Polymerization: Tuning the Length of Nanofibers

Jatish Kumar et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Synthesis and Predetermined Supramolecular Chirality of Carbohydrate-Functionalized Perylene Bisimide Derivatives

Ke-Rang Wang et al.

Chemistry-An Asian Journal (2015)

Article Chemistry, Organic

The molecular recognition controlled stereomutation cycle in a dynamic helical assembly

Mohit Kumar et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

Review Polymer Science

Perylenediimide-cored dendrimers and their bioimaging and gene delivery applications

Kelan Liu et al.

PROGRESS IN POLYMER SCIENCE (2015)

Article Chemistry, Multidisciplinary

Regioselective Functionalization of Core- Persubstituted Perylene Diimides

Wan Yue et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

Article Chemistry, Physical

Circularly Polarized Luminescence in Chiral Aggregates: Dependence of Morphology on Luminescence Dissymmetry

Jatish Kumar et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2014)

Article Chemistry, Multidisciplinary

Homotropic and heterotropic allosteric regulation of supramolecular chirality

Mohit Kumar et al.

CHEMICAL SCIENCE (2014)

Article Chemistry, Multidisciplinary

Fluorescent Nanoparticle Delivered dsRNA Toward Genetic Control of Insect Pests

Bicheng He et al.

ADVANCED MATERIALS (2013)

Article Chemistry, Organic

Multivalent glycoclusters constructed by chiral self-assembly of mannose functionalized perylene bisimide

Ke-Rang Wang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

Article Chemistry, Multidisciplinary

Self-Assembled Sugar-Substituted Perylene Diimide Nanostructures with Homochirality and High Gas Sensitivity

Jianchen Hu et al.

ADVANCED FUNCTIONAL MATERIALS (2012)

Article Chemistry, Multidisciplinary

Chiral self-assembly of lactose functionalized perylene bisimides as multivalent glycoclusters

Ke-Rang Wang et al.

CHEMICAL COMMUNICATIONS (2012)

Article Chemistry, Multidisciplinary

Chiral J-Aggregates of Atropo-Enantiomeric Perylene Bisimides and Their Self-Sorting Behavior

Zengqi Xie et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Chemistry, Multidisciplinary

Pathway-Dependent Self-Assembly of Perylene Diimide/Peptide Conjugates in Aqueous Medium

Yaron Tidhar et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

Article Chemistry, Multidisciplinary

Chiral Self-Recognition and Self-Discrimination of Strapped Perylene Bisimides by pi-Stacking Dimerization

Marina M. Safont-Sempere et al.

CHEMISTRY-A EUROPEAN JOURNAL (2010)

Article Chemistry, Applied

Association phenomena of a chiral perylene derivative in solution and in poly(ethylene) dispersion

Andrea Pucci et al.

REACTIVE & FUNCTIONAL POLYMERS (2010)

Article Chemistry, Organic

Chiral Water-Soluble Perylenediimides

Cordula D. Schmidt et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2009)

Article Chemistry, Multidisciplinary

A black perylene bisimide super gelator with an unexpected J-type absorption band

Frank Wuerthner et al.

ADVANCED MATERIALS (2008)

Article Chemistry, Multidisciplinary

A chiral pinwheel supramolecular network driven by the assembly of PTCDI and melamine

Fabien Silly et al.

CHEMICAL COMMUNICATIONS (2008)

Article Chemistry, Multidisciplinary

Exciton trapping in π-conjugated materials:: A quantum-chemistry-based protocol applied to perylene bisimide dye aggregates

Reinhold F. Fink et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2008)

Article Chemistry, Multidisciplinary

Effects of bay substituents on the racemization barriers of perylene bisimides: Resolution of atropo-enantiomers

Peter Osswald et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Organic

Perylene bisimide atropisomers:: Synthesis, resolution, and stereochemical assignment

Peter Osswald et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

Article Chemistry, Organic

Suzuki coupling reaction of 1,6,7,12-tetrabromoperylene bisimide

WF Qiu et al.

ORGANIC LETTERS (2006)

Article Chemistry, Multidisciplinary

Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes

F Würthner et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Synthesis of n-type perylene bisimide derivatives and their orthogonal self-assembly with p-type oligo(p-phenylene vinylene)s

J van Herrikhuyzen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Multidisciplinary

Photoinduced electron transfer in hydrogen-bonded oligo(p-phenylene vinylene)-perylene bisimide chiral assemblies

APHJ Schenning et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002)