Thioether- and sulfone-functionalized dibenzopentalenes as n-channel semiconductors for organic field-effect transistors

Mathias Hermann, Ruihan Wu, David C. Grenz, Daniel Kratzert, Hanying Li and Birgit Esser

J. Mater. Chem. C, 2018, 6, 5420
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The effect of two types of dibenzoannulation of pentalene on molecular energies and magnetically induced currents

Marija Baranac-Stojanović and Milovan Stojanović

Phys. Chem. Chem. Phys., 2019, 21, 3250
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Facile preparation and investigation of the properties of single molecular POSS-based white-light-emitting hybrid materials using click chemistry

Gang Zhao, Yakun Zhu, Shanyi Guang, Fuyou Ke and Hongyao Xu

New J. Chem., 2018, 42, 555
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Indenofluorenes for organic optoelectronics: the dance of fused five- and six-membered rings enabling structural versatility

Ayse Can, Antonio Facchetti and Hakan Usta

J. Mater. Chem. C, 2022, 10, 8496
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Single-molecule conductance of dibenzopentalenes: antiaromaticity and quantum interference

Maximilian Schmidt, Daniel Wassy, Mathias Hermann, M. Teresa González, Nicolás Agräit, Linda A. Zotti, Birgit Esser and Edmund Leary

Chem. Commun., 2021, 57, 745
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Enantiopure nanohoops through racemic resolution of diketo[n]CPPs by chiral derivatization as precursors to DBP[n]CPPs

Daniel Wassy, Mathias Hermann, Jan S. Wössner, Lucas Frédéric, Grégory Pieters and Birgit Esser

Chem. Sci., 2021, 12, 10150
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Dibenzo[a,e]pentalenophanes: Bending a Non‐Alternant Hydrocarbon

Mathias Hermann, Daniel Wassy, Daniel Kratzert and Birgit Esser

Chemistry A European J, 2018, 24, 7374
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N‐Heterocycle‐Fused Pentalenes by a Gold‐Catalyzed Annulation of Diethynyl‐Quinoxalines and ‐Phenazines

Kohei Sekine, Fabian Stuck, Jürgen Schulmeister, Thomas Wurm, Dominik Zetschok, Frank Rominger, Matthias Rudolph and A. Stephen K. Hashmi

Chemistry A European J, 2018, 24, 12515
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[n]Cyclodibenzopentalenes as Antiaromatic Curved Nanocarbons with High Strain and Strong Fullerene Binding

Jan S. Wössner, Daniel Wassy, Andrej Weber, Marcel Bovenkerk, Mathias Hermann, Maximilian Schmidt and Birgit Esser

J. Am. Chem. Soc., 2021, 143, 12244
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Theoretical prediction of thermal and electronic properties of metal-organic frameworks

Harmeet Kaur, Shashank Sundriyal, Virendra Kumar, Amit L. Sharma, Ki-Hyun Kim, Bo Wang and Akash Deep

Journal of Industrial and Engineering Chemistry, 2019, 80, 136
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Stereoselective Insertion of Benzynes into Lawsones: Synthesis of Biologically Important Benzannulated Bicyclo[3.3.0]octanes

A. Suresh Kumar, Guguloth Thirupathi, G. Surendra Reddy and Dhevalapally B. Ramachary

Chemistry A European J, 2019, 25, 1177
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NIR‐Absorbing π‐Extended Azulene: Non‐Alternant Isomer of Terrylene Bisimide

Bartłomiej Pigulski, Kazutaka Shoyama and Frank Würthner

Angew Chem Int Ed, 2020, 59, 15908
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Conjugated Nanohoops with Dibenzo[a,e]pentalenes as Nonalternant and Antiaromatic π-Systems

Birgit Esser, Jan S. Wössner and Mathias Hermann

Synlett, 2022, 33, 737
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Engineering the packing structure of thioether‐ and sulfone‐substituted dibenzo[a,e]pentalenes by pentafluorophenyl substitution

Mathias Hermann, David C. Grenz and Birgit Esser

J of Physical Organic Chem, 2023, 36
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Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives

Maozhong Miao, Mengchao Jin, Panpan Chen, Lei Wang, Shouzhi Zhang and Hongjun Ren

Org. Lett., 2019, 21, 5957
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s-Indacene Revisited: Modular Synthesis and Modulation of Structures and Molecular Orbitals of Hexaaryl Derivatives

Shun-Jie Jhang, Jayabalan Pandidurai, Ching-Piao Chu, Hirokazu Miyoshi, Yuta Takahara, Masahito Miki, Hikaru Sotome, Hiroshi Miyasaka, Shreyam Chatterjee, Rumi Ozawa, Yutaka Ie, Ichiro Hisaki, Chia-Lin Tsai, Yen-Ju Cheng and Yoshito Tobe

J. Am. Chem. Soc., 2023, 145, 4716
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A DFT Study of the Modulation of the Antiaromatic and Open‐Shell Character of Dibenzo[a,f]pentalene by Employing Three Strategies: Additional Benzoannulation, BN/CC Isosterism, and Substitution

Marija Baranac‐Stojanović

Chemistry A European J, 2019, 25, 9747
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Structure–Property Relationships in Unsymmetric Bis(antiaromatics): Who Wins the Battle between Pentalene and Benzocyclobutadiene?

Péter J. Mayer, Ouissam El Bakouri, Tamás Holczbauer, Gergely F. Samu, Csaba Janáky, Henrik Ottosson and Gábor London

J. Org. Chem., 2020, 85, 5158
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Increased Antiaromaticity through Pentalene Connection in [n]Cyclo-1,5-dibenzopentalenes

Jan S. Wössner, Julia Kohn, Daniel Wassy, Mathias Hermann, Stefan Grimme and Birgit Esser

Org. Lett., 2022, 24, 983
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Cations and Anions of Dibenzo[a,e]pentalene and Reduction of a Dibenzo[a,e]pentalenophane

Mathias Hermann, Tobias Böttcher, Marcel Schorpp, Sabine Richert, Daniel Wassy, Ingo Krossing and Birgit Esser

Chemistry A European J, 2021, 27, 4964
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Conjugated Nanohoop Polymers based on Antiaromatic Dibenzopentalenes for Charge Storage in Organic Batteries

Philipp Seitz, Manik Bhosale, Luisa Rzesny, Anselm Uhlmann, Jan S. Wössner, Robin Wessling and Birgit Esser

Angewandte Chemie, 2023, 135
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Syntheses and Properties of Hole-Transporting Biindenofluorenes

Himanshu Sharma, Ankita, Vishal Mittal, Upendra Kumar Pandey and Soumyajit Das

Org. Lett., 2024, 26, 2617
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Synthesis and Characterization of Dinaphtho[2,1-a:2,3-f]pentalene: A Stable Antiaromatic/Quinoidal Hydrocarbon Showing Appropriate Carrier Mobility in the Amorphous Layer

Koki Horii, Akira Nogata, Yusuke Mizuno, Haruna Iwasa, Mitsuharu Suzuki, Ken-ichi Nakayama, Akihito Konishi and Makoto Yasuda

Chemistry Letters, 2022, 51, 325
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Unsymmetrical Thienopentalenes: Synthesis, Optoelectronic Properties, and (Anti)aromaticity Analysis

Tamás Gazdag, Péter J. Mayer, Péter Pál Kalapos, Tamás Holczbauer, Ouissam El Bakouri and Gábor London

ACS Omega, 2022, 7, 8336
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Isolable Dibenzo[a,e]disilapentalene with a Dichotomic Reactivity toward CO2

Bochao Su, Arseni Kostenko, Shenglai Yao and Matthias Driess

J. Am. Chem. Soc., 2020, 142, 16935
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Intramolecular Charge Transfer in Antiaromatic Donor/Acceptor‐Fused s‐Indacenes

Isabella S. Demachkie, Michael P. Miller, Gabrielle I. Warren, Joshua E. Barker, Eric T. Strand, Lev N. Zakharov and Michael M. Haley

Angew Chem Int Ed, 2025, 64
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An Exploration of Substituent Effects on the Photophysical Properties of Monobenzopentalenes

Tamás Gazdag, Enikő Meiszter, Péter J. Mayer, Tamás Holczbauer, Henrik Ottosson, Andrew B. Maurer, Maria Abrahamsson and Gábor London

ChemPhysChem, 2024, 25
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Breathing New Life into Nonalternant Hydrocarbon Chemistry: Syntheses and Properties of Polycyclic Hydrocarbons Containing Azulene, Pentalene, and Heptalene Frameworks

Akihito Konishi and Makoto Yasuda

Chemistry Letters, 2021, 50, 195
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Low‐lying LUMO Boosts Conductance in Antiaromatic Dibenzopentalene Versus Aromatic Analogues

Maximilian Schmidt, Lydia Abellán Vicente, M. Teresa González, Linda A. Zotti, Birgit Esser and Edmund Leary

Chemistry A European J, 2024, 30
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Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

Cyril Aumaitre and Jean‐François Morin

The Chemical Record, 2019, 19, 1142
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Control of Homocoupling Versus Reduction in Titanium(III)‐Mediated Radical Opening of Styrene Oxides

José A. González‐Delgado and Jesús F. Arteaga

Eur J Org Chem, 2019, 2019, 7864
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Antiaromatic Covalent Organic Frameworks Based on Dibenzopentalenes

Josefine Sprachmann, Tommy Wachsmuth, Manik Bhosale, David Burmeister, Glen J. Smales, Maximilian Schmidt, Zdravko Kochovski, Niklas Grabicki, Robin Wessling, Emil J. W. List-Kratochvil, Birgit Esser and Oliver Dumele

J. Am. Chem. Soc., 2023, 145, 2840
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Chiral Dibenzopentalene‐Based Conjugated Nanohoops through Stereoselective Synthesis

Mathias Hermann, Daniel Wassy, Julia Kohn, Philipp Seitz, Martin U. Betschart, Stefan Grimme and Birgit Esser

Angewandte Chemie, 2021, 133, 10775
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Enhancement of Antiaromatic Character via Additional Benzoannulation into Dibenzo[a,f]pentalene: Syntheses and Properties of Benzo[a]naphtho[2,1-f]pentalene and Dinaphtho[2,1-a,f]pentalene

Akihito Konishi, Yui Okada, Ryohei Kishi, Masayoshi Nakano and Makoto Yasuda

J. Am. Chem. Soc., 2019, 141, 560
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Gram-Scale Synthesis of Dibenzo[a,e]pentalenes from Trialkyl(phenylethynyl)silanes via Organosodium Intermediates

Ayane Sato and Takuya Kuwabara

J. Org. Chem., 2025, 90, 9258
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Effect of Annulation Pattern on the Antiaromaticity of Thioether‐ and Sulfone‐Substituted Dinaphthopentalenes

Mathias Hermann, Silas M. A. Battisti and Birgit Esser

Asian J Org Chem, 2025, 14
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NIR‐Absorbing π‐Extended Azulene: Non‐Alternant Isomer of Terrylene Bisimide

Bartłomiej Pigulski, Kazutaka Shoyama and Frank Würthner

Angewandte Chemie, 2020, 132, 16042
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Chiral Dibenzopentalene‐Based Conjugated Nanohoops through Stereoselective Synthesis

Mathias Hermann, Daniel Wassy, Julia Kohn, Philipp Seitz, Martin U. Betschart, Stefan Grimme and Birgit Esser

Angew Chem Int Ed, 2021, 60, 10680
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Dibenzo[a,e]pentalenes with Low-Lying LUMO Energy Levels as Potential n-Type Materials

David C. Grenz, Maximilian Schmidt, Daniel Kratzert and Birgit Esser

J. Org. Chem., 2018, 83, 656
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Conjugated Nanohoop Polymers based on Antiaromatic Dibenzopentalenes for Charge Storage in Organic Batteries

Philipp Seitz, Manik Bhosale, Luisa Rzesny, Anselm Uhlmann, Jan S. Wössner, Robin Wessling and Birgit Esser

Angew Chem Int Ed, 2023, 62
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Generating antiaromaticity in polycyclic conjugated hydrocarbons by thermally selective skeletal rearrangements at interfaces

Elena Pérez-Elvira, Ana Barragán, Qifan Chen, Diego Soler-Polo, Ana Sánchez-Grande, Diego J. Vicent, Koen Lauwaet, José Santos, Pingo Mutombo, Jesús I. Mendieta-Moreno, Bruno de la Torre, José M. Gallego, Rodolfo Miranda, Nazario Martín, Pavel Jelínek, José I. Urgel and David Écija

Nat. Synth, 2023, 2, 1159
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Synthesis and Properties of Conjugated Nanohoops Incorporating Dibenzo[a,e]pentalenes: [2]DBP[12]CPPs

Daniel Wassy, Manuel Pfeifer and Birgit Esser

J. Org. Chem., 2020, 85, 34
DOI: 10.1021/acs.joc.9b01195

Intramolecular Charge Transfer in Antiaromatic Donor/Acceptor‐Fused s‐Indacenes

Isabella S. Demachkie, Michael P. Miller, Gabrielle I. Warren, Joshua E. Barker, Eric T. Strand, Lev N. Zakharov and Michael M. Haley

Angewandte Chemie, 2025, 137
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An Acceptor-Substituted N-Heterocyclic ortho-Quinodimethane: Pushing the Boundaries of Polarization in Donor–Acceptor-Substituted Polyenes

Jama Ariai and Urs Gellrich

J. Am. Chem. Soc., 2024, 146, 32859
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5,10-Diiododibenzo[a,e]pentalene

Natsumi Ohara, Chinatsu Ogiwara and Takuya Kuwabara

Molbank, 2024, 2024, M1937
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Stable Monoareno-pentalenes with Two Olefinic Protons

Péter J. Mayer and Gábor London

Org. Lett., 2023, 25, 42
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