4.3 Article

Closed-shell and open-shell dual nature of singlet diradical compounds

相关参考文献

注意:仅列出部分参考文献,下载原文获取全部文献信息。
Article Chemistry, Multidisciplinary

On-Surface Synthesis of Chiral Graphene Nanoribbon Segments via the Quarter-Anthryl on Au(111) Surface

Hui Zhang et al.

Summary: This study reports the fabrication of quarteranthene and its chiral graphene nanoribbon segment on Au(111) substrate. The chemical structure of the fabricated products on the Au(111) substrate is confirmed through bond-resolved scanning tunneling microscopy, noncontact atomic force microscopy characterization, and density functional theory calculations. The analysis reveals that the lateral-extended structures are acquired via the linkage of the hydrocarbon quarter-anthryl. Additionally, several strategies are used to modulate the yield of quarteranthene and its lateral-extended products. These findings provide new insights into the lateral extension strategy on metal substrates and offer another possible fabrication strategy of chiral graphene nanoribbons on the relative inert Au(111) substrate.

ADVANCED MATERIALS INTERFACES (2023)

Article Chemistry, Multidisciplinary

Synthesis and Characterization of peri-Heptacene on a Metallic Surface

Kalyan Biswas et al.

Summary: This study reports the successful on-surface synthesis of the largest pristine member of the n-PA family, peri-heptacene, on an Au(111) substrate under ultra-high vacuum conditions. High-resolution scanning tunneling microscopy and theoretical simulations provide insights into the chemical structure of this previously elusive compound. Scanning tunneling spectroscopy reveals that peri-heptacene exhibits an antiferromagnetic open-shell singlet ground state and a singlet-triplet spin-flip inelastic excitation with an effective exchange coupling of 49 meV.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Review Chemistry, Organic

π-Extended peri-Acenes: Recent Progress in Synthesis and Characterization

M. R. Ajayakumar et al.

Summary: Nanographenes with open-shell character, especially those with parallel zigzag edges, have potential applications in organic nanoelectronics and spintronics. However, their reactive edges make their synthesis challenging. Recent developments have allowed the synthesis of pi-extended PAs in solution, but further research is needed to overcome stability and solubility challenges.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Chemistry, Multidisciplinary

A Stable [4,3]Peri-acene Diradicaloid: Synthesis, Structure, and Electronic Properties

Jun-Jian Shen et al.

Summary: In this study, a derivative of peri-acene was successfully isolated and characterized for its stability, structure, and electronic properties. The compound demonstrated a reasonable stability with a long half-life time and exhibited unique electronic characteristics when compared to other related acene derivatives.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

Unravelling the Open-Shell Character of Peripentacene on Au(111)

Ana Sanchez-Grande et al.

Summary: Polycyclic aromatic hydrocarbons (PAHs) are organic compounds with multiple fused aromatic rings, some of which exhibit open-shell magnetic ground states. Recent research has focused on the synthesis and study of acene and fused acene (periacene) families, with experimental evidence of a magnetic ground state reported for isolated peripentacene molecules. This discovery contributes to a better understanding of organic compounds with magnetic properties, particularly in the development of carbon-based spintronic devices.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2021)

Article Chemistry, Multidisciplinary

Antiaromatic Dicyclopenta[b,g]/[a,f]naphthalene Isomers Showing an Open-Shell Singlet Ground State with Tunable Diradical Character

Tingting Xu et al.

Summary: This article reports the successful synthesis of two relatively stable, core-expanded indacene isomers and characterizes them through various analytical methods. Both molecules are globally antiaromatic, with one showing stronger antiaromaticity and larger diradical character.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

Article Chemistry, Multidisciplinary

Dicyclopentaannelated Hexa-peri-hexabenzocoronenes with a Singlet Biradical Ground State

Qiang Chen et al.

Summary: The synthesis of two dicyclopentaannelated hexa-peri-hexabenzocoronene (PHBC) regioisomers demonstrates unique electronic structures, with one stable molecule and the other only characterized in situ with high reactivity. These molecules exhibit low energy gaps and significant singlet biradical characters, opening up new avenues for open-shell polycyclic aromatic hydrocarbons (PAHs).

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Persistent peri-Heptacene: Synthesis and In Situ Characterization

M. R. Ajayakumar et al.

Summary: The synthesis of a previously unknown peri-heptacene (7-PA) with kinetically protected zigzag edges and high stability under inert conditions has been achieved. This compound displays open-shell and tetraradical characteristics, making it a potential modular approach for constructing next-generation n-peri-Acenes.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

Spin-Spin Interactions in One-Dimensional Assemblies of a Cumulene-Based Singlet Biradical

Yasukazu Hirao et al.

Summary: The synthesis of phenalenyl-endcapped [5]cumulene as a cumulene-based singlet biradical and the spin correlation changes of one-dimensional aggregates are discussed. The introduction of bulky substituents into the appropriate positions led to the formation of a one-dimensional chain assembly, with increased bond length alternation of the cumulene chain and improved overlapping of the phenalenyl rings at lower temperatures. Variable-temperature Raman spectroscopy and magnetic susceptibility measurements revealed the decoupling of a localized spin pair at low temperatures, and the emergence of a continuum spin system involving intra- and intermolecular spin-spin interactions in the one-dimensional chain.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Multidisciplinary

A Tale of Two Isomers: Enhanced Antiaromaticity/Diradical Character versus Deleterious Ring-Opening of Benzofuran-fused s-Indacenes and Dicyclopenta[b,g]naphthalenes

Joshua E. Barker et al.

Summary: The effects of fusing benzofurans and naphthalene to s-indacene to control antiaromaticity and diradical character were examined, showing different outcomes based on synthesis methods and unexpected ring-opening reactions during final steps. Increased oxygen electronegativity in the syn-fused derivatives enhanced antiaromatic core, while increased diradical character in syn-IIDBF resulted from rearomatization of the naphthalene unit.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Physical

On-Surface Synthesis and Characterization of Super-nonazethrene

Elia Turco et al.

Summary: This study reports the on-surface synthesis of the largest zethrene homologue to date, super-nonazethrene, which exhibits an open-shell singlet ground state and a strong intramolecular magnetic exchange coupling. The results provide unprecedented access to large, open-shell zethrene compounds for scanning probe measurements, with potential applications in molecular spintronics.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2021)

Article Chemistry, Organic

Dipyrene-Fused Dicyclopenta[a,f]naphthalenes

Jason Melidonie et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Cove-Edged Nanographenes with Localized Double Bonds

Yanwei Gu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Article Chemistry, Multidisciplinary

Molecule Isomerism Modulates the Diradical Properties of Stable Singlet Diradicaloids

Joshua E. Barker et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Duality of Reactivity of a Biradicaloid Compound with an o-Quinodimethane Scaffold

Keisuke Sahara et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Tailoring Magnetic Features in Zigzag-Edged Nanographenes by Controlled Diels-Alder Reactions

M. R. Ajayakumar et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Organic

Cover Image

Justin J. Dressler et al.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2020)

Article Chemistry, Multidisciplinary

Monoradicals and Diradicals of Dibenzofluoreno[3,2-b]fluorene Isomers: Mechanisms of Electronic Delocalization

Hideki Hayashi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Revisiting indeno[2,1-c]fluorene synthesis while exploring the fully conjugateds-indaceno[2,1-c:6,5-c′]difluorene

Himanshu Sharma et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

On-surface synthesis of super-heptazethrene

Shantanu Mishra et al.

CHEMICAL COMMUNICATIONS (2020)

Article Chemistry, Multidisciplinary

Stable Diindeno-Fused Corannulene Regioisomers with Open-Shell Singlet Ground States and Large Diradical Characters

Ru-Qiang Lu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Article Chemistry, Multidisciplinary

A Concise Synthetic Strategy for Accessing Ambient Stable Bisphenalenyls toward Achieving Electroactive Open-Shell π-Conjugated Materials

Caleb M. Wehrmann et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Diindeno-Fused Dibenzo[a,h]anthracene and Dibenzo[c,l]chrysene: Syntheses, Structural Analyses, and Properties

Siva Senthil Kumar Boominathan et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

Review Chemistry, Multidisciplinary

Do Diradicals Behave Like Radicals?

Thijs Stuyver et al.

CHEMICAL REVIEWS (2019)

Article Chemistry, Multidisciplinary

Synthesis and Properties of Benzo-Fused Indeno[2,1-c]fluorenes

Tanguy Jousselin-Oba et al.

CHEMISTRY-AN ASIAN JOURNAL (2019)

Article Chemistry, Multidisciplinary

Fluoreno[2,1-a]fluorene: an ortho-naphthoquinodimethane-based system with partial diradical character

Allison S. Hacker et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

peri-Acenoacenes

Yanwei Gu et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

A Peri-tetracene Diradicaloid: Synthesis and Properties

Yong Ni et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

Graphene-like Molecules with Four Zigzag Edges

Yanwei Gu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Organic

Cethrene: The Chameleon of Woodward-Hoffmann Rules

Tomas Solomek et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Toward Full Zigzag-Edged Nanographenes: peri-Tetracene and Its Corresponding Circumanthracene

M. R. Ajayakumar et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Dimethylcethrene: A Chiroptical Diradicaloid Photoswitch

Prince Ravat et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Thiophene and its sulfur inhibit indenoindenodibenzothiophene diradicals from low-energy lying thermal triplets

Justin J. Dressler et al.

NATURE CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Diazuleno-s-indacene Diradicaloids: Syntheses, Properties, and Local (anti)Aromaticity Shift from Neutral to Dicationic State

Qing Jiang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Article Chemistry, Multidisciplinary

5,14-Diaryldiindeno[2,1-f:1 ',2 '-j]picene: A New Stable [7]Helicene with a Partial Biradical Character

Ya-Chu Hsieh et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Article Chemistry, Multidisciplinary

Efficient Singlet Fission and Triplet-Pair Emission in a Family of Zethrene Diradicaloids

Steven Lukman et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

Article Chemistry, Organic

Synthesis and Properties of Quinoidal Fluorenofluorenes

Joshua E. Barker et al.

ORGANIC LETTERS (2017)

Article Chemistry, Multidisciplinary

Synthesis of the Unknown Indeno[1,2-a]fluorene Regioisomer: Crystallographic Characterization of Its Dianion

Justin J. Dressler et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Modern zethrene chemistry

Pan Hu et al.

CANADIAN JOURNAL OF CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

A Stable Saddle-Shaped Polycyclic Hydrocarbon with an Open-Shell Singlet Ground State

Ji Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Cethrene: A Helically Chiral Biradicaloid Isomer of Heptazethrene

Prince Ravat et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Super-heptazethrene

Wangdong Zeng et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Extended Bis(benzothia)quinodimethanes and Their Dications: From Singlet Diradicaloids to Isoelectronic Structures of Long Acenes

Shaoqiang Dong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Organic

Diindenopyrenes: Extended 1,6-and 1,8-Pyrenoquinodimethanes with Singlet Diradical Characters

Daijiro Hibi et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Higher Order π-Conjugated Polycyclic Hydrocarbons with Open-Shell Singlet Ground State: Nonazethrene versus Nonacene

Rui Huang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Article Chemistry, Multidisciplinary

Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals

Gabriel E. Rudebusch et al.

NATURE CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Zethrene and Dibenzozethrene: Masked Biradical Molecules?

Ya-Chu Hsieh et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

Closing the Nanographene Gap: Surface-Assisted Synthesis of Peripentacene from 6,6'-Bipentacene Precursors

Cameron Rogers et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Article Chemistry, Multidisciplinary

The Longest Acenes

Holger F. Bettinger et al.

CHEMICAL RECORD (2015)

Article Chemistry, Organic

Stable 7,14-Disubstituted-5,12-Dithiapentacenes with Quinoidal Conjugation

Qun Ye et al.

ORGANIC LETTERS (2014)

Article Chemistry, Multidisciplinary

Benz[c] indeno[2,1-a] fluorene: a 2,3-naphthoquinodimethane incorporated into an indenofluorene frame

Hirokazu Miyoshi et al.

CHEMICAL SCIENCE (2014)

Article Chemistry, Multidisciplinary

Heptacene: Increased Persistence of a 4n+2 π-Electron Polycyclic Aromatic Hydrocarbon by Oxidation to the 4n π-Electron Dication

Ralf Einholz et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Indeno[2,1-b]fluorene: A 20-π-Electron Hydrocarbon with Very Low-Energy Light Absorption

Akihiro Shimizu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Review Chemistry, Multidisciplinary

Diradicals

Manabu Abe

CHEMICAL REVIEWS (2013)

Article Chemistry, Physical

Comparative study of diradical characters and third-order nonlinear optical properties of linear/cyclic acenes versus phenylenes

Shabbir Muhammad et al.

INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY (2013)

Article Chemistry, Organic

Indeno[2,1-c]fluorene: A New Electron-Accepting Scaffold for Organic Electronics

Aaron G. Fix et al.

ORGANIC LETTERS (2013)

Article Chemistry, Multidisciplinary

Revisiting zethrene: synthesis, reactivity and semiconductor properties

Liang Shan et al.

CHEMICAL SCIENCE (2013)

Article Chemistry, Multidisciplinary

Synthesis, Crystal Structures, and Properties of 6,12-Diaryl-Substituted Indeno[1,2-b]fluorenes

Jun-ichi Nishida et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Chemistry, Physical

Diradical Character View of Singlet Fission

Takuya Minami et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2012)

Article Chemistry, Multidisciplinary

6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs

Daniel T. Chase et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Kinetically Blocked Stable Heptazethrene and Octazethrene: Closed-Shell or Open-Shell in the Ground State?

Yuan Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2012)

Article Chemistry, Multidisciplinary

Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes

Daniel T. Chase et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Indeno[2,1-a]fluorene: An Air-Stable ortho-Quinodimethane Derivative

Akihiro Shimizu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Synthesis and Structural Characterization of Crystalline Nonacenes

Balaji Purushothaman et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Physical

Focal Point Analysis of the Singlet-Triplet Energy Gap of Octacene and Larger Acenes

Balazs Hajgato et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2011)

Article Chemistry, Multidisciplinary

Products and Mechanism of Acene Dimerization. A Computational Study

Sanjio S. Zade et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Multidisciplinary

Soluble and Stable Heptazethrenebis(dicarboximide) with a Singlet Open-Shell Ground State

Zhe Sun et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2011)

Article Chemistry, Multidisciplinary

Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes

Tsun-Cheng Wu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

Article Chemistry, Physical

Singlet Diradical Character from Experiment

Kenji Kamada et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2010)

Article Chemistry, Multidisciplinary

Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekule Structures

Akihito Konishi et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Multidisciplinary

Alternating Covalent Bonding Interactions in a One-Dimensional Chain of a Phenalenyl-Based Singlet Biradical Molecule Having Kekule Structures

Akihiro Shimizu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2010)

Article Chemistry, Organic

Soluble and Stable Zethrenebis(dicarboximide) and Its Quinone

Zhe Sun et al.

ORGANIC LETTERS (2010)

Article Chemistry, Multidisciplinary

Resonance Balance Shift in Stacks of Delocalized Singlet Biradicals

Akihiro Shimizu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

Article Chemistry, Physical

Open-Shell Ground State of Polyacenes: A Valence Bond Study

Zexing Qu et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2009)

Article Chemistry, Multidisciplinary

Synthesis, Stability, and Photochemistry of Pentacene, Hexacene, and Heptacene: A Matrix Isolation Study

Rajib Mondal et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2009)

Article Chemistry, Physical

Electronic ground state of higher acenes

De-en Jiang et al.

JOURNAL OF PHYSICAL CHEMISTRY A (2008)

Article Chemistry, Inorganic & Nuclear

Biradicaloid character of phenalenyl-based aromatic compounds with a small HOMO-LUMO gap

T Kubo et al.

POLYHEDRON (2005)

Article Chemistry, Multidisciplinary

Synthesis, intermolecular interaction, and semiconductive behavior of a delocalized singlet biradical hydrocarbon

T Kubo et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

Article Chemistry, Multidisciplinary

Oligoacenes: Theoretical prediction of open-shell singlet diradical ground states

M Bendikov et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)