4.4 Article

Dictating Packing and Interactions of Perylene Bisimides within Cyclophane Structures in the Solid State

Related references

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

Preferential molecular recognition of heterochiral guests within a cyclophane receptor

Manuel Weh et al.

Summary: The discrimination of enantiomers by natural receptors is a well-established phenomenon, but the number of synthetic receptors with enantioselective molecular recognition capability is limited. In this study, a cyclophane composed of homochiral perylene bisimide (PBI) units was shown to preferentially bind [5]helicene of opposite helicity compared to the PBI units of the host. The enantio-differentiation of this molecular receptor for heterochiral guests can be utilized for the enrichment of specific bimolecular complex. The design of synthetic supramolecular receptors capable of enantioselective molecular recognition is challenging, and this study presents a novel approach using perylene bisimide-based receptors.

NATURE COMMUNICATIONS (2023)

Article Chemistry, Multidisciplinary

The Pink Box: Exclusive Homochiral Aromatic Stacking in a Bis-perylene Diimide Macrocycle

Samuel E. Penty et al.

Summary: This work demonstrates the importance of chiral complementarity in aromatic stacking interactions for optimizing the chiroptical and electrochemical properties of perylene diimides (PDIs). Through the construction of a dynamic bis-PDI macrocycle, the homochiral PDI-PDI K-K stacking interactions can be exclusively activated, leading to enhanced optoelectronic performance of PDIs.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

Article Multidisciplinary Sciences

Steering the multiexciton generation in slip-stacked perylene dye array via exciton coupling

Yongseok Hong et al.

Summary: This study investigates the role of exciton coupling, exciton delocalization, and excimer state in facilitating the singlet fission process using a slip-stacked perylene bisimide array. The results provide insights into the structure-property relationship in dye arrays and have implications for the design of organic photonic and photovoltaic materials.

NATURE COMMUNICATIONS (2022)

Article Chemistry, Multidisciplinary

A highly contorted push-pull naphthalenediimide dimer and evidence of intramolecular singlet exciton fission

Deepak Bansal et al.

Summary: This study reports the intramolecular singlet fission phenomenon in a push-pull cyclophane structure of NDI, which is not possible in individual NDI chromophores. Experimental and electronic structure calculations confirm the existence of the T-T pair state.

CHEMICAL SCIENCE (2022)

Review Chemistry, Multidisciplinary

Extendedtight-bindingquantum chemistry methods

Christoph Bannwarth et al.

Summary: This review discusses a family of atomistic, mostly quantum chemistry based semiempirical methods for describing large molecules in gas and condensed phase. These methods are derived from a density functional perturbation expansion and emphasize parameter availability for almost the entire periodic table, with improvements in atomic orbital basis set and interaction treatments. The methods are consistent with accurate gas phase theoretical reference data and have been extended for electronic spectra and response properties.

WILEY INTERDISCIPLINARY REVIEWS-COMPUTATIONAL MOLECULAR SCIENCE (2021)

Article Chemistry, Physical

Robust and Efficient Implicit Solvation Model for Fast Semiempirical Methods

Sebastian Ehlert et al.

Summary: A robust and efficient method is proposed to implicitly account for solvation effects in modern semiempirical quantum mechanics and force fields. The method based on the analytical linearized Poisson-Boltzmann (ALPB) model shows good performance over a broad range of systems and applications, with high accuracy in hydration free energy calculation.

JOURNAL OF CHEMICAL THEORY AND COMPUTATION (2021)

Article Chemistry, Multidisciplinary

Diastereoselective formation of homochiral flexible perylene bisimide cyclophanes and their hybrids with fullerenes

Iris Solymosi et al.

Summary: The properties of cyclophanes are dramatically influenced by the number of PBIs and their geometric arrangement, particularly the co-facial pi-pi interactions. Two-PBI cyclophanes show strong physico-chemical characteristics governed by co-facial pi-pi interactions, while three-PBI cyclophanes exhibit less favorable stacking. The integration of hydrophobic or hydrophilic fullerenes into cyclophanes allows for unprecedented diastereoselective formation of homochiral pairs, offering new possibilities in the field.

CHEMICAL SCIENCE (2021)

Article Chemistry, Multidisciplinary

The Green Box: An Electronically Versatile Perylene Diimide Macrocyclic Host for Fullerenes

Timothy A. Barendt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Robust Atomistic Modeling of Materials, Organometallic, and Biochemical Systems

Sebastian Spicher et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Backbone-Directed Self-Assembly of Interlocked Molecular Cyclic Metalla[3]Catenanes

Ting Feng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Materials Science, Multidisciplinary

Crystal Engineering of 1D Exciton Systems Composed of Single- and Double-Stranded Perylene Bisimide J-Aggregates

Matthias Stolte et al.

ADVANCED OPTICAL MATERIALS (2020)

Article Chemistry, Multidisciplinary

Shape-Selective Synthesis of Pentacene Macrocycles and the Effect of Geometry on Singlet Fission

Harrison M. Bergman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Review Chemistry, Multidisciplinary

Molecular insights and concepts to engineer singlet fission energy conversion devices

Ruben Casillas et al.

ENERGY & ENVIRONMENTAL SCIENCE (2020)

Article Chemistry, Physical

Automated exploration of the low-energy chemical space with fast quantum chemical methods

Philipp Pracht et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2020)

Article Crystallography

Crystal Structures of Two Perylenediimides: A Study of Bay-Substitution

Nuray Esra Aksakal et al.

JOURNAL OF CHEMICAL CRYSTALLOGRAPHY (2019)

Article Chemistry, Multidisciplinary

Controlling Singlet Fission by Molecular Contortion

Felisa S. Conrad-Burton et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Physical

Steric Interactions Impact Vibronic and Vibrational Coherences in Perylenediimide Cyclophanes

Jonathan D. Schultz et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2019)

Article Chemistry, Multidisciplinary

A Water-Soluble Perylene Bisimide Cyclophane as a Molecular Probe for the Recognition of Aromatic Alkaloids

Meike Sapotta et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

Discrete Dimers of Redox-Active and Fluorescent Perylene Diimide-Based Rigid Isosceles Triangles in the Solid State

Siva Krishna Mohan Nalluri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Engineering, Electrical & Electronic

Heteroatom Bay-Annulated Perylene Bisimides: New Materials for Organic Field Effect Transistors

Ravindra Kumar Gupta et al.

ACS APPLIED ELECTRONIC MATERIALS (2019)

Article Chemistry, Multidisciplinary

Singlet Fission Involves an Interplay between Energetic Driving Force and Electronic Coupling in Perylenediimide Films

Aaron K. Le et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Multidisciplinary Sciences

Hollow organic capsules assemble into cellular semiconductors

Boyuan Zhang et al.

NATURE COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Singlet fission in self-assembled PDI nanocrystals

Christoph Schierl et al.

NANOSCALE (2018)

Article Chemistry, Multidisciplinary

Anion- and Solvent-Induced Rotary Dynamics and Sensing in a Perylene Diimide [3]Catenane

Timothy A. Barendt et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Review Chemistry, Multidisciplinary

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

Frank Wuerthner et al.

CHEMICAL REVIEWS (2016)

Article Chemistry, Physical

Access to Triplet Excited State in Core-Twisted Perylenediimide

Kalaivanan Nagarajan et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2016)

Article Chemistry, Multidisciplinary

A Perylene Bisimide Cyclophane as a Turn-On and Turn-Off Fluorescence Probe

Peter Spenst et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Self-Assembled Microdisk Lasers of Perylenediimides

Zhenyi Yu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Multidisciplinary

SHELXT - Integrated space-group and crystal-structure determination

George M. Sheldrick

ACTA CRYSTALLOGRAPHICA A-FOUNDATION AND ADVANCES (2015)

Article Chemistry, Multidisciplinary

Crystal structure refinement with SHELXL

George M. Sheldrick

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY (2015)

Article Chemistry, Physical

Maximizing Singlet Fission by Intermolecular Packing

Linjun Wang et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2014)

Article Chemistry, Multidisciplinary

Structure-property relationships for 1,7-diphenoxy-perylene bisimides in solution and in the solid state

Angel J. Jimenez et al.

CHEMICAL SCIENCE (2014)

Article Chemistry, Organic

Macrocyclic Dyads Based on C60 and Perylenediimides Connected by Click Chemistry

Sara Pla et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2014)

Article Chemistry, Multidisciplinary

Effect of the Ortho Alkylation of Perylene Bisimides on the Alignment and Self-Assembly Properties

Debarshi Dasgupta et al.

CHEMISTRYOPEN (2014)

Article Chemistry, Multidisciplinary

Redox-switchable Intramolecular π-π-Stacking of Perylene Bisimide Dyes in a Cyclophane

Felix Schlosser et al.

ADVANCED MATERIALS (2013)

Article Chemistry, Multidisciplinary

Excitation energy migration in covalently linked perylene bisimide macrocycles

Felix Schlosser et al.

CHEMICAL SCIENCE (2012)

Article Chemistry, Multidisciplinary

Effect of the Damping Function in Dispersion Corrected Density Functional Theory

Stefan Grimme et al.

JOURNAL OF COMPUTATIONAL CHEMISTRY (2011)

Software Review Chemistry, Multidisciplinary

OLEX2: a complete structure solution, refinement and analysis program

Oleg V. Dolomanov et al.

JOURNAL OF APPLIED CRYSTALLOGRAPHY (2009)

Article Chemistry, Multidisciplinary

Cyclophanes of perylene tetracarboxylic diimide with different substituents at bay positions

Junqian Feng et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Review Chemistry, Physical

Ground- and excited-state pinched cone equilibria in calix[4]arenes bearing two perylene bisimide dyes

Catharina Hippius et al.

JOURNAL OF PHYSICAL CHEMISTRY C (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, Multidisciplinary

Beyond exciton theory: A time-dependent DFT and Franck-Condon study of perylene diimide and its chromophoric dimer

Aurora E. Clark et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Cyclization and catenation directed by molecular self-assembly

Wei Wang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2006)

Article Chemistry, Physical

Accurate Coulomb-fitting basis sets for H to Rn

F Weigend

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2006)

Review Chemistry, Multidisciplinary

Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures

F Wurthner

CHEMICAL COMMUNICATIONS (2004)