☆ 4.8 Article

Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups

CHEMICAL SCIENCE (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Hybrids of Benzene and Borazine Azaborines

Y. A. N. N. I. K. APPIARIUS et al.

Summary: 1,2-azaborinines, formed by replacing two neighboring carbon atoms in benzene with boron and nitrogen atoms, exhibit increased aromaticity compared to borazine. Experimental analysis of bond lengths, resonance stabilization energies, NMR shifts, and reactivities against electrophiles confirms this. Azaborinines, both monocyclic and polycyclic, have potential applications in materials science, pharmacology, and analytics due to their unique chemical, physical, and optical properties introduced by the polar B-N-unit.

CHEMIE IN UNSERER ZEIT (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Efficient Narrowband Circularly Polarized Light Emitters Based on 1,4-B,N-embedded Rigid Donor-Acceptor Helicenes

Fangyuan Zhang et al.

Summary: This article introduces a design strategy to achieve narrow-band emission for applicable circularly polarized luminescence (CPL) active materials in ultrahigh-definition CP-OLEDs, by exploiting intramolecular donor-acceptor interactions between nitrogen and boron atoms. Single- and double-helicenes with 1,4-B,N-embedded configurationally stable structure were successfully synthesized, showing unprecedentedly narrow fluorescence and CPL bands, along with high fluorescence quantum yields.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Editorial Material Nanoscience & Nanotechnology

Materials for chiral light control

Jeanne Crassous et al.

Summary: Solution-processable semiconductors based on small molecules, polymers or halide perovskites combine sustainable manufacturing with exceptional optoelectronic properties that can be chemically tailored to achieve flexible and highly efficient optoelectronic and photonic devices. A new exciting research direction is the study of the influence of chirality on light-matter interactions in these soft materials and its exploitation for the simultaneous control of charge, spin and light. In this Viewpoint, researchers working on different types of chiral semiconductors discuss the most interesting directions in this rapidly expanding field.

NATURE REVIEWS MATERIALS (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Diradical B/N-Doped Polycyclic Hydrocarbons

Jiaxiang Guo et al.

Summary: We report the synthesis of B/N-type organic diradicaloids with atom-precise control over open-shell nature through quinoidal pi-extension of a B/N-heterocycle. These diradicaloids exhibit modulated (anti)aromaticity and enhanced diradical characters compared with all-carbon analogues, and display intriguing properties such as magnetic activities and highly red-shifted absorptions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Review Chemistry, Medicinal

Circularly polarized luminescence of helicenes: A data-informed insight

Matteo Cei et al.

Summary: In this short review, the authors collected the dissymmetry factors associated with the first Cotton effect of the ECD spectrum for 170 [n]-helicenes. They found reasonable correlations between luminescence and absorption, suggesting similarity in the stereochemistry of the ground and emitting excited states for most helicenes. These results can be helpful in rationalizing chiroptical data and designing new helicene structures with desired CPL properties.

CHIRALITY (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Circularly Polarized Luminescence of [6]Helicenes through Excited-State Intramolecular Proton Transfer

Dominik Goebel et al.

Summary: By synthesizing a [6]helicene with ESIPT structural units, we have successfully combined CPL and ESIPT features into a single molecule. Our study shows that this compound exhibits strong CPL response and significant red-shifted emission, making it a promising candidate for applications in optoelectronics.

HELVETICA CHIMICA ACTA (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Enhanced N-directed electrophilic C-H borylation generates BN-[5]- and [6]helicenes with improved photophysical properties

Kang Yuan et al.

Summary: This article develops an enhanced N-directed electrophilic C-H borylation methodology to access azaborine containing helicenes. The borylation process utilizes the protonation of an aminoborane with bistriflimidic acid. The synthesized helicenes show increased strain and racemization half-life, as well as improved fluorescence efficiency due to the incorporation of BN units.

CHEMICAL SCIENCE (2022)

Add to Collection

Article Chemistry, Physical

BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State

Yannik Appiarius et al.

Summary: Boron-nitrogen substitutions have a strong impact on the optical properties of polycyclic aromatic hydrocarbons (PAHs), but the observed properties also depend on intermolecular interactions. This study compared a thiophene-flanked BN-pyrene with its all-carbon analogue in solution and in the solid state, and found clear differences in their optical properties and crystal packing motifs.

JOURNAL OF PHYSICAL CHEMISTRY C (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Enhanced Optical Properties of Azaborole Helicenes by Lateral and Helical Extension

Felix Full et al.

Summary: This article describes the synthesis and characterization of laterally extended azabora[5]-, [6]- and -[7]helicenes using N-heteroaromatic and dibenzo[g,p]chrysene building blocks. The enlargement of the pi-conjugated systems of azaborole helicenes led to compounds with improved optical properties. The combination of lateral and helical extensions resulted in a compound with a high luminescence quantum yield and dissymmetry factor, superior to its non-extended congener. The study suggests that helical and lateral extensions are viable strategies to enhance the features of azaborole helicenes.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

Add to Collection

Review Chemistry, Multidisciplinary

Quantifying the Overall Efficiency of Circularly Polarized Emitters

Lorenzo Arrico et al.

Summary: This study introduces a new concept of CPL brightness (B-CPL), which takes into consideration the absorption extinction coefficient and quantum yield in addition to the g(lum) factor, to comprehensively evaluate the efficiency of CPL emitters. By calculating B-CPL values for over 180 compounds and analyzing the data distribution for main classes of CPL molecular emitters, this tool can aid in contextualizing new CPL active compounds and guiding the selection of molecular systems for specific CPL applications.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Carbo[n]helicenes Restricted to Enantiomerize: An Insight into the Design Process of Configurationally Stable Functional Chiral PAHs

Prince Ravat

Summary: The interconversion of enantiomers is a key stereodynamic feature of carbo[n]helicenes, with the Gibbs activation energy determining their configurational stability. This minireview provides an overview of the mechanism, recent developments, and factors affecting the enantiomerization of [n]helicenes, aiming to accelerate the design process of configurationally stable functional chiral molecules based on helicene substructures. Additionally, misconceptions and irregularities in the recent literature on terms such as racemization and enantiomerization, as well as the calculation of activation parameters for [n]helicenes and related compounds, are addressed.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Single-Molecule Conductance of 1,4-Azaborine Derivatives as Models of BN-doped PAHs

Lucia Palomino-Ruiz et al.

Summary: The study found that the single-molecule conductance of BN-acene-like derivatives is comparable to that of all-carbon anthracene compounds, indicating that B-N doping could be used to stabilize and characterize larger acenes for molecular electronics applications. This conclusion is supported by state-of-the-art transport calculations.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices

Julian Full et al.

Summary: Helically chiral compounds with one and two boron atoms were synthesized using a modular approach, showing exceptional configurational stability and fluorescence properties. The compounds are proposed as primary structures of extended helices, with potential applications in materials science.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Add to Collection

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)

Add to Collection

Article Chemistry, Multidisciplinary

B,N-Embedded Double Hetero[7]helicenes with Strong Chiroptical Responses in the Visible Light Region

Ji-Kun Li et al.

Summary: This study presents unprecedented B,N-embedded double hetero[7]helicenes with excellent chiroptical properties, high absorption dissymmetry factors, and tunable circularly polarized luminescence, opening up new possibilities for the development of high-performance chiroptical materials in the future.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Add to Collection

Review Chemistry, Analytical

Lateral-Type Spin-Photonics Devices: Development and Applications

Nozomi Nishizawa et al.

Summary: Lateral-type spin-photonic devices have advantages in circularly polarized light applications including compactness, standalone nature, room temperature operation, high circular polarization emission, polarization controllability, and are widely used in various fields and potentially for biological diagnosis.

MICROMACHINES (2021)

Add to Collection

Article Materials Science, Multidisciplinary

Tuning the aggregation behaviour of BN-coronene diimides with imide substituents and their performance in devices (OLEDs and OFETs)

Jonas Hoffmann et al.

Summary: By extending the core with two BN units instead of two CC units, significant bathochromic shifts, higher molar extinction coefficients, and beneficial luminescence properties can be achieved. However, different substitution motifs at the imide position have a substantial impact on aggregation of coronene diimides, resulting in differences in optical properties in the solid state and performance in organic devices.

JOURNAL OF MATERIALS CHEMISTRY C (2021)

Add to Collection

Article Materials Science, Multidisciplinary

BN-Substituted coronene diimide donor-acceptor-donor triads: photophysical, (spectro)-electrochemical studies and Lewis behavior

Jonas Hoffmann et al.

Summary: The study investigates the electronic properties of boron/nitrogen substituted polyaromatic hydrocarbons by tuning their properties through substitution at the B and/or N atoms. BN-PAH analogues showed enhanced absorption/emission properties and luminescence quantum yields compared to all-carbon analogues. The unique donor-acceptor-donor motif based on BN units exhibited interesting electronic behavior and solvent-dependent luminescence properties.

JOURNAL OF MATERIALS CHEMISTRY C (2021)

Add to Collection

Article Chemistry, Organic

From a 1,2-azaborinine to large BN-PAHs via electrophilic cyclization: synthesis, characterization and promising optical properties

Yannik Appiarius et al.

Summary: A convergent synthetic route towards boron-nitrogen containing polycyclic aromatic hydrocarbons (BN-PAHs) was developed, allowing the synthesis of six derivatives with high quantum yields. The route avoids the need for substituted PAH precursors and instead builds up BN-PAHs solely from easily accessible monocycles. The emission properties of the derivatives were dependent on the connectivity of the rings, and one derivative exhibited significantly redshifted emission due to excimer formation.

ORGANIC CHEMISTRY FRONTIERS (2021)

Add to Collection

Article Chemistry, Organic

Synthesis, Properties, and Reactivity of Bis-BN Phenanthrenes: Stepwise Bromination of the Main Scaffold

Lingjian Zi et al.

ORGANIC LETTERS (2020)

Add to Collection

Article Nanoscience & Nanotechnology

Multicolor Circularly Polarized Photoluminescence and Electroluminescence with 1,2-Diaminecyclohexane Enantiomers

Xu-Feng Luo et al.

ACS APPLIED MATERIALS & INTERFACES (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene

Alberto Abengozar et al.

CHEMICAL COMMUNICATIONS (2020)

Add to Collection

Article Chemistry, Organic

BN-Phenanthrenes: Synthesis, Reactivity, and Optical Properties

Chen Zhang et al.

ORGANIC LETTERS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Enantioenriched Helicenes and Helicenoids Containing Main-Group Elements (B, Si, N, P)

Kais Dhbaibi et al.

CHEMICAL REVIEWS (2019)

Add to Collection

Review Chemistry, Multidisciplinary

Late-stage functionalization of BN-heterocycles

Cameron R. McConnell et al.

CHEMICAL SOCIETY REVIEWS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Stable Enantiomers Displaying Thermally Activated Delayed Fluorescence: Efficient OLEDs with Circularly Polarized Electroluminescence

Meng Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of functionalized helical BN-benzo[c]phenanthrenes

Alberto Abengozar et al.

CHEMICAL COMMUNICATIONS (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Azabora[5]helicene Charge-Transfer Dyes Show Efficient and Spectrally Variable Circularly Polarized Luminescence

Zoe Dominguez et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis, Structures, and Optical Properties of Azahelicene Derivatives and Unexpected Formation of Azahepta[8]circulenes

Fengkun Chen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

Add to Collection

Article Chemistry, Physical

TADDOL-Derived Cationic Phosphonites: Toward an Effective Enantioselective Synthesis of [6]Helicenes via Au-Catalyzed Alkyne Hydroarylation

Leo D. M. Nicholls et al.

ACS CATALYSIS (2018)

Add to Collection

Article Chemistry, Physical

Combined Experimental and Theoretical Study on Circular Dichroism and Circularly Polarized Luminescence of Configurationally Robust D-3-Symmetric Triple Pentahelicene

Hiroki Tanaka et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Symmetry-based rational design for boosting chiroptical responses

Hiroki Tanaka et al.

COMMUNICATIONS CHEMISTRY (2018)

Add to Collection

Review Chemistry, Physical

Circularly Polarized Luminescence and Circular Dichroisms in Small Organic Molecules: Correlation between Excitation and Emission Dissymmetry Factors

Hiroki Tanaka et al.

CHEMPHOTOCHEM (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis and Chiroptical Properties of Hexa-, Octa-, and Deca-azaborahelicenes: Influence of Helicene Size and of the Number of Boron Atoms

Chengshuo Shen et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Add to Collection

Article Chemistry, Organic

Oxygen-Bridged Diphenylnaphthylamine as a Scaffold for Full-Color Circularly Polarized Luminescent Materials

Hidetaka Nishimura et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Add to Collection

Article Biochemistry & Molecular Biology

Substitution determination of Fmoc-substituted resins at different wavelengths

Stefan Eissler et al.

JOURNAL OF PEPTIDE SCIENCE (2017)

Add to Collection

Article Chemistry, Multidisciplinary

A Boron Protecting Group Strategy for 1,2-Azaborines

Andrew W. Baggett et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Add to Collection

Article Chemistry, Organic

Control over the Emission Properties of [5]Flelicenes Based on the Symmetry and Energy Levels of Their Molecular Orbitals

Hiromu Kubo et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Organic

Configurational Stability of [5]Helicenes

Prince Ravat et al.

ORGANIC LETTERS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Intense blue circularly polarized luminescence from helical aromatic esters

Dong-Qiang He et al.

CHEMICAL COMMUNICATIONS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Facile Two-Step Synthesis of 1,10-Phenanthroline-Derived Polyaza[7]helicenes with High Fluorescence and CPL Efficiency

Takashi Otani et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Two-Step Synthesis of Boron-Fused Double Helicenes

Takazumi Katayama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Add to Collection

Article Chemistry, Organic

Synthesis and Properties of Sila[n]helicenes via Dehydrogenative Silylation of C-H Bonds under Rhodium Catalysis

Masahito Murai et al.

ORGANIC LETTERS (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene

Takashi Matsuno et al.

CHEMICAL COMMUNICATIONS (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Chimerical Pyrene-Based [7]Helicenes as Twisted Polycondensed Aromatics

Michal Buchta et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Circularly Polarized Luminescence from Simple Organic Molecules

Esther M. Sanchez-Carnerero et al.

CHEMISTRY-A EUROPEAN JOURNAL (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Late-Stage Functionalization of 1,2-Dihydro-1,2-azaborines via Regioselective Iridium-Catalyzed C-H Borylation: The Development of a New N,N-Bidentate Ligand Scaffold

Andrew W. Baggett et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Add to Collection

Article Chemistry, Physical

Triplet-Energy Control of Polycyclic Aromatic Hydrocarbons by BN Replacement: Development of Ambipolar Host Materials for Phosphorescent Organic Light-Emitting Diodes

Sigma Hashimoto et al.

CHEMISTRY OF MATERIALS (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Two BN lsosteres of Anthracene: Synthesis and Characterization

Jacob S. A. Ishibashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

Add to Collection

Article Chemistry, Multidisciplinary

Induction of Circularly Polarized Electroluminescence from an Achiral Light-Emitting Polymer via a Chiral Small-Molecule Dopant

Ying Yang et al.

ADVANCED MATERIALS (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Rapid Access to Dibenzohelicenes and their Functionalized Derivatives

Andrej Jancarik et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Add to Collection

Review Chemistry, Multidisciplinary

One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

Marc Gingras

CHEMICAL SOCIETY REVIEWS (2013)

Add to Collection

Article Chemistry, Physical

Theoretical and Experimental Studies of Circular Dichroism of Mono-and Diazonia[6]helicenes

Yoshito Nakai et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2013)

Add to Collection

Article Optics

Circularly polarized light detection by a chiral organic semiconductor transistor

Ying Yang et al.

NATURE PHOTONICS (2013)

Add to Collection

Article Chemistry, Organic

Facile Synthetic Route to Highly Luminescent Sila[7]helicene

Hiromi Oyama et al.

ORGANIC LETTERS (2013)

Add to Collection

Review Chemistry, Multidisciplinary

Forty years of Clar's aromatic pi-sextet rule

Miquel Sola

FRONTIERS IN CHEMISTRY (2013)

Add to Collection

Review Chemistry, Multidisciplinary

Recent Advances in Azaborine Chemistry

Patrick G. Campbell et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Intermolecular Oxidative Annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes

Kiyohiko Goto et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Add to Collection

Review Chemistry, Multidisciplinary

Helicenes: Synthesis and Applications

Yun Shen et al.

CHEMICAL REVIEWS (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Azaboradibenzo[6]helicene: Carrier Inversion Induced by Helical Homochirality

Takuji Hatakeyama et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Add to Collection

Article Physics, Applied

Optical communication of spin information between light emitting diodes

R. Farshchi et al.

APPLIED PHYSICS LETTERS (2011)

Add to Collection

Article Chemistry, Multidisciplinary

A Hybrid Organic/Inorganic Benzene

Adam J. V. Marwitz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Add to Collection

Review Chemistry, Inorganic & Nuclear

Luminescent chiral lanthanide(III) complexes as potential molecular probes

Gilles Muller

DALTON TRANSACTIONS (2009)

Add to Collection

Article Chemistry, Multidisciplinary

Enantioselective regulation of a metal complex in reversible binding to serum albumin: dynamic helicity inversion signalled by circularly polarised luminescence

Craig P. Montgomery et al.

CHEMICAL COMMUNICATIONS (2008)

Add to Collection

Review Chemistry, Multidisciplinary

Nucleus-independent chemical shifts (NICS) as an aromaticity criterion

ZF Chen et al.

CHEMICAL REVIEWS (2005)

Add to Collection

Article Chemistry, Multidisciplinary

Circular dichroism of helicenes investigated by time-dependent density functional theory

F Furche et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2000)

Add to Collection

© Peeref 2019-2024. All rights reserved.