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RESEARCH PAPER · Chemistry - A European Journal · 2008

New Reactions of a Dibenzo[a,e]pentalene

Masaichi Saito, Michio Nakamura, Tomoyuki Tajima

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New Reactions of a Dibenzo[a,e]pentaleneOriginalAlkali and alkaline earth metals7Alkali and alkaline-earth metals10Novel Reactions of Steric Encumbered 1,4-Dilithio-1,3-butadiene with Group 14 Electrophiles: Formation and Structure of Stable Dihydroxygermole8An Extremely Simple Dibenzopentalene Synthesis from 2‐Bromo‐1‐ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities126Versatile Synthesis of Pentalene Derivatives via the Pd-Catalyzed Homocoupling of Haloenynes163Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons87Synthesis and Reactions of Dibenzo[a,e]pentalenes103Synthesis and Electronic Properties of Extended, Fused-Ring Aromatic Systems Containing Multiple Pentalene Units87Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors196Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors70Indeno[1,2‐b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes309Indeno[1,2‐b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes103Synthesis of a Pentalene Centered Polycyclic Fused System45Indeno[2,1‐a]fluorene: An Air‐Stable ortho‐Quinodimethane Derivative258Indeno[2,1‐a]fluorene: An Air‐Stable ortho‐Quinodimethane Derivative70Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton16Electron‐Accepting 6,12‐Diethynylindeno[1,2‐b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties182Electron‐Accepting 6,12‐Diethynylindeno[1,2‐b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties47Development and Application of Polycyclic Conjugated Systems Bearing a Pentalene Skeleton1Molecular Structure and Electronic State of the Dibenzo[a,e]pentalene Anion Radical22Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes2756,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs345Dihalo-Substituted Dibenzopentalenes: Their Practical Synthesis and Transformation to Dibenzopentalene Derivatives65Electron Acceptors Based on Functionalizable Cyclopenta[hi]aceanthrylenes and Dicyclopenta[de,mn]tetracenes152Electron Acceptors Based on an All‐Carbon Donor–Acceptor Copolymer55Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen‐Bonding Interactions of meso‐Imidazolyl Groups39Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen‐Bonding Interactions of meso‐Imidazolyl Groups18Electron Acceptors Based on an All‐Carbon Donor–Acceptor Copolymer21C–H activation route to dibenzo[a,e]pentalenes: annulation of arylacetylenes promoted by PdCl2–AgOTf–o-chloranil115Indeno[2,1-c]fluorene: A New Electron-Accepting Scaffold for Organic Electronics151Orthogonal Functionalization of Cyclopenta[hi]aceanthrylenes29Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes103Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry52Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry19Pentalene – von hochreaktiven Antiaromaten zu Ausgangsmaterialien für die Materialwissenschaften32Pentalenes—From Highly Reactive Antiaromatics to Substrates for Material Science121Synthesis, Structure, and Reactivity of Lewis Base Stabilized Plumbacyclopentadienylidenes34Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers13Benzo[f]benzo[5,6]indolo[3,2-b]indole: a stable unsubstituted 4nπ-electron acene with an antiaromatic 1,4-diazapentalene core45Rubicene: a molecular fragment of C 70 for use in organic field-effect transistors55Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues63Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues24Facile Synthesis of Dibenzopentalene Dianions and Their Application as New π‐Extended Ligands19Transformation of octadehydrodibenzo[12]annulene to benzonaphthopentalene by successive nucleophilic and electrophilic transannular cyclizations7Non‐Alternant Non‐Benzenoid A romatic C ompounds: Past, Present, and Future141Dianthraceno[a,e]pentalenes: synthesis, crystallographic structures and applications in organic field-effect transistors82Thienoacene‐Fused Pentalenes: Syntheses, Structures, Physical Properties and Applications for Organic Field‐Effect Transistors45Dibenzopentalenes and Related Compounds1π‐Extended Pentalenes: The Revival of the Old Compound from New Standpoints57Deliberate Charge Conjugation Symmetry Breaking for π-Conjugated Electron Acceptor Design4One-Shot Double Amination of Sondheimer–Wong Diynes: Synthesis of Photoluminescent Dinaphthopentalenes23Planar Cyclopenta‐Fused Polycyclic Arenes14Diacenopentalene dicarboximides as new n-type organic semiconductors for field-effect transistors42Recent Developments in Fulvene and Heterofulvene Chemistry11Pentaleno[1,2-a:4,5′]diacenaphthylenes: Uniquely Stabilized Pentalene Derivatives46Fast construction of dianthraceno[a,e]pentalenes for OPV applications18Reactions of Dilithium Dibenzopentalenides with Cr(CO)3(CH3CN)3: Unexpected Formation of a Cubic Tetramer of an Anionic Hydrodibenzopentalenyl Complex2Formation of Dibenzopentalene-linking Polymers under the Two-zone CVD and Wet Conditions7Creation of Exotic π-Electron Systems by Introduction of Heavy Elements and Expansion of the Concept of Aromaticity18Polycyclic Arene Synthesis by Annulative π-Extension237Design and synthesis of high performance π-conjugated materials through antiaromaticity and quinoid strategy for organic field-effect transistors104Antiaromatic character of cycloheptatriene-bis-annelated indenofluorene framework mainly originated from heptafulvene segment56TfOH-promoted Classical Nazarov-type Cyclization of Benzofulvenes: Synthesis of Polycyclic 5H,10′H-spiro[benzo[k]phenanthridine-5,6′-dibenzopentalenes]7Antiaromatic Dicyclopenta[b,g]/[a,f]naphthalene Isomers Showing an Open-Shell Singlet Ground State with Tunable Diradical Character75Manifestations of Antiaromaticity in Organic Materials: Case Studies of Cyclobutadiene, Borole, and Pentalene68Synthesis, structure and catalytic properties of Pdii-based bimetallic complexes with ferrocenecarboxylic acid6Antiaromatic Covalent Organic Frameworks Based on Dibenzopentalenes70Indenoannulated Tridecacyclene: An All‐Carbon Seven‐Stage Redox‐Amphoter13Reversible formation of tetraphenylpentalene, a room temperature stable antiaromatic hydrocarbon55,10-Diiododibenzo[a,e]pentalene2Cyclopentannulated Decacyclenes as Carbon‐Based Multistage Electron Acceptors3Gram-Scale Synthesis of Dibenzo[ a , e ]pentalenes from Trialkyl(phenylethynyl)silanes via Organosodium Intermediates3Lithium-mediated mechanochemical annulative dimerization of diarylacetylenes for synthesis of 1,4-dihydrodinaphthopentalenes1Streamlined synthesis of functionalized dibenzo[ a , e ]pentalenes through potassium-mediated cyclization and late-stage thianthrenation0

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  1. Alkali and alkaline earth metals

    Annual Reports Section A (Inorganic Chemistry) · 2008-01-01

    Michael S. Hill

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  2. Alkali and alkaline-earth metals

    Annual Reports Section A (Inorganic Chemistry) · 2009-01-01

    Michael S. Hill

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  3. Novel Reactions of Steric Encumbered 1,4-Dilithio-1,3-butadiene with Group 14 Electrophiles: Formation and Structure of Stable Dihydroxygermole

    Heterocycles · 2009-01-01

    Masaichi Saito, Michio Nakamura, Tomoyuki Tajima

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  4. An Extremely Simple Dibenzopentalene Synthesis from 2‐Bromo‐1‐ethynylbenzenes Using Nickel(0) Complexes: Construction of Its Derivatives with Various Functionalities

    Chemistry - A European Journal · 2009-02-02

    Takeshi Kawase, Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo

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  5. Versatile Synthesis of Pentalene Derivatives via the Pd-Catalyzed Homocoupling of Haloenynes

    Journal of the American Chemical Society · 2009-02-06

    Zerubba U. Levi, T. Don Tilley

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  6. Intramolecular Reductive Double Cyclization of o,o′-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons

    Organic Letters · 2009-06-18

    Hongyu Zhang, Takashi Karasawa, Hiroshi Yamada, Atsushi Wakamiya, Shigehiro Yamaguchi

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  7. Synthesis and Reactions of Dibenzo[a,e]pentalenes

    Symmetry · 2010-04-21

    Masaichi Saito

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  8. Synthesis and Electronic Properties of Extended, Fused-Ring Aromatic Systems Containing Multiple Pentalene Units

    Journal of the American Chemical Society · 2010-07-27

    Zerubba U. Levi, T. Don Tilley

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  9. Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors

    Angewandte Chemie International Edition · 2010-09-10

    Takeshi Kawase, Takeru Fujiwara, Chitoshi Kitamura, Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Shoji Shinamura, Hiroki Mori, Eigo Miyazaki, Kazuo Takimiya

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  10. Dinaphthopentalenes: Pentalene Derivatives for Organic Thin‐Film Transistors

    Angewandte Chemie · 2010-09-10

    Takeshi Kawase, Takeru Fujiwara, Chitoshi Kitamura, Akihito Konishi, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo, Shoji Shinamura, Hiroki Mori, Eigo Miyazaki, Kazuo Takimiya

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  11. Indeno[1,2‐b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes

    Angewandte Chemie International Edition · 2010-12-22

    Daniel T. Chase, Bradley D. Rose, Sean P. McClintock, Lev N. Zakharov, Michael M. Haley

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  12. Indeno[1,2‐b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes

    Angewandte Chemie · 2010-12-22

    Daniel T. Chase, Bradley D. Rose, Sean P. McClintock, Lev N. Zakharov, Michael M. Haley

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  13. Synthesis of a Pentalene Centered Polycyclic Fused System

    Organic Letters · 2011-02-24

    Xiaodong Yin, Yongjun Li, Yongjun Li, Yulan Zhu, Yu‐He Kan, Yuliang Li, Yuliang Li, Daoben Zhu

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  14. Indeno[2,1‐a]fluorene: An Air‐Stable ortho‐Quinodimethane Derivative

    Angewandte Chemie International Edition · 2011-06-15

    Akihiro Shimizu, Yoshito Tobe

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  15. Indeno[2,1‐a]fluorene: An Air‐Stable ortho‐Quinodimethane Derivative

    Angewandte Chemie · 2011-06-15

    Akihiro Shimizu, Yoshito Tobe

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  16. Fluorescent 3-Methylene-2,3-Dihydrochalcogenophenes Incorporated in a Rigid Dibenzobarrelene Skeleton

    Organic Letters · 2011-06-21

    Akihiko Ishii, Yuki Yamaguchi, Norio Nakata

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  17. Electron‐Accepting 6,12‐Diethynylindeno[1,2‐b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties

    Angewandte Chemie International Edition · 2011-09-26

    Daniel T. Chase, Aaron G. Fix, Bradley D. Rose, Christopher D. Weber, Shunpei Nobusue, Chelsea E. Stockwell, Lev N. Zakharov, Mark C. Lonergan, Michael M. Haley

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  18. Electron‐Accepting 6,12‐Diethynylindeno[1,2‐b]fluorenes: Synthesis, Crystal Structures, and Photophysical Properties

    Angewandte Chemie · 2011-09-26

    Daniel T. Chase, Aaron G. Fix, Bradley D. Rose, Christopher D. Weber, Shunpei Nobusue, Chelsea E. Stockwell, Lev N. Zakharov, Mark C. Lonergan, Michael M. Haley

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  19. Development and Application of Polycyclic Conjugated Systems Bearing a Pentalene Skeleton

    Journal of Synthetic Organic Chemistry Japan · 2012-01-01

    Takeshi Kawase

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  20. Molecular Structure and Electronic State of the Dibenzo[a,e]pentalene Anion Radical

    Chemistry - An Asian Journal · 2012-01-13

    Masaichi Saito, Yoko Hashimoto, Tomoyuki Tajima, Kazuya Ishimura, Shigeru Nagase, Mao Minoura

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  21. Gold‐Catalyzed Synthesis of Dibenzopentalenes – Evidence for Gold Vinylidenes

    Advanced Synthesis & Catalysis · 2012-02-23

    A. Stephen K. Hashmi, M. Wieteck, Ingo Braun, Pascal Nösel, Linda S. Jongbloed, Matthias Rudolph, Frank Röminger

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  22. 6,12-Diarylindeno[1,2-b]fluorenes: Syntheses, Photophysics, and Ambipolar OFETs

    Journal of the American Chemical Society · 2012-06-14

    Daniel T. Chase, Aaron G. Fix, Seok Ju Kang, Bradley D. Rose, Christopher D. Weber, Yu Zhong, Lev N. Zakharov, Mark C. Lonergan, Colin P. Nuckolls, Michael M. Haley

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  23. Dihalo-Substituted Dibenzopentalenes: Their Practical Synthesis and Transformation to Dibenzopentalene Derivatives

    Organic Letters · 2012-07-16

    Feng Xu, Lifen Peng, Akihiro Orita, Junzo Otera

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  24. Electron Acceptors Based on Functionalizable Cyclopenta[hi]aceanthrylenes and Dicyclopenta[de,mn]tetracenes

    Journal of the American Chemical Society · 2012-08-31

    Jordan D. Wood, Jessica L. Jellison, Aaron D. Finke, Lichang Wang, Kyle N. Plunkett

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  25. Electron Acceptors Based on an All‐Carbon Donor–Acceptor Copolymer

    Angewandte Chemie International Edition · 2012-10-29

    Jessica L. Jellison, Che‐Hsiung Lee, Xinju Zhu, Jordan D. Wood, Kyle N. Plunkett

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  26. Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen‐Bonding Interactions of meso‐Imidazolyl Groups

    Angewandte Chemie International Edition · 2012-11-04

    Hirotaka Mori, Young Mo Sung, Byung Sun Lee, Dongho Kim, Atsuhiro Osuka

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  27. Antiaromatic Hexaphyrins and Octaphyrins Stabilized by the Hydrogen‐Bonding Interactions of meso‐Imidazolyl Groups

    Angewandte Chemie · 2012-11-05

    Hirotaka Mori, Young Mo Sung, Byung Sun Lee, Dongho Kim, Atsuhiro Osuka

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  28. Electron Acceptors Based on an All‐Carbon Donor–Acceptor Copolymer

    Angewandte Chemie · 2012-11-28

    Jessica L. Jellison, Che‐Hsiung Lee, Xinju Zhu, Jordan D. Wood, Kyle N. Plunkett

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  29. C–H activation route to dibenzo[a,e]pentalenes: annulation of arylacetylenes promoted by PdCl2–AgOTf–o-chloranil

    Chemical Science · 2013-01-01

    Takehisa Maekawa, Yasutomo Segawa, Kenichiro Itami

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

    Organic Letters · 2013-03-05

    Aaron G. Fix, Parker E. Deal, Chris L. Vonnegut, Bradley D. Rose, Lev N. Zakharov, Michael M. Haley

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  31. Orthogonal Functionalization of Cyclopenta[hi]aceanthrylenes

    Organic Letters · 2013-03-05

    Che-Hsiung Lee, Kyle N. Plunkett

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  32. Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes

    Journal of the American Chemical Society · 2013-06-28

    Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, Tienan Jin

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  33. Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry

    Angewandte Chemie International Edition · 2013-10-01

    Heng Li, Baosheng Wei, Ling Xu, Wen‐Xiong Zhang, Zhenfeng Xi

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  34. Barium Dibenzopentalenide as a Main‐Group Metal η8 Complex: Facile Synthesis from 1,4‐Dilithio‐1,3‐butadienes and Ba[N(SiMe3)2]2, Structural Characterization, and Reaction Chemistry

    Angewandte Chemie · 2013-10-01

    Heng Li, Baosheng Wei, Ling Xu, Wen‐Xiong Zhang, Zhenfeng Xi

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  35. Pentalene – von hochreaktiven Antiaromaten zu Ausgangsmaterialien für die Materialwissenschaften

    Angewandte Chemie · 2013-10-11

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  36. Pentalenes—From Highly Reactive Antiaromatics to Substrates for Material Science

    Angewandte Chemie International Edition · 2013-10-11

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  37. Synthesis, Structure, and Reactivity of Lewis Base Stabilized Plumbacyclopentadienylidenes

    Chemistry - A European Journal · 2013-11-15

    Masaichi Saito, Tomoki Akiba, Misumi Kaneko, Toshiaki Kawamura, Minori Abe, Masahiko Hada, Mao Minoura

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  38. Antiaromaticity in Nonbenzenoid Oligoarenes and Ladder Polymers

    Topics in current chemistry · 2014-01-01

    Rebecca R. Parkhurst, Timothy Manning Swager

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  39. Benzo[f]benzo[5,6]indolo[3,2-b]indole: a stable unsubstituted 4nπ-electron acene with an antiaromatic 1,4-diazapentalene core

    Chemical Communications · 2014-01-01

    Li Qiu, Xuhui Zhuang, Na Zhao, Xiao Wang, Zengjian An, Zhenggang Lan, Xiaobo Wan

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  40. Rubicene: a molecular fragment of C 70 for use in organic field-effect transistors

    Journal of Materials Chemistry C · 2014-01-01

    Hyunbok Lee, Yue Zhang, Lei Zhang, Timothy Mirabito, Edmund K. Burnett, Stefan Trahan, Ali Reza Mohebbi, Stefan C. B. Mannsfeld, Fred Wudl, Alejandro L. Briseño

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  41. Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues

    Angewandte Chemie International Edition · 2014-05-05

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  42. Synthesis and Properties of a New Class of Fully Conjugated Azahexacene Analogues

    Angewandte Chemie · 2014-05-05

    Wan Yue, Sabin–Lucian Suraru, David Bialas, Matthias Müller, Frank Würthner

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  43. Facile Synthesis of Dibenzopentalene Dianions and Their Application as New π‐Extended Ligands

    Chemistry - A European Journal · 2014-05-07

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  44. Transformation of octadehydrodibenzo[12]annulene to benzonaphthopentalene by successive nucleophilic and electrophilic transannular cyclizations

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  45. Non‐Alternant Non‐Benzenoid A romatic C ompounds: Past, Present, and Future

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  46. Dianthraceno[a,e]pentalenes: synthesis, crystallographic structures and applications in organic field-effect transistors

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  47. Thienoacene‐Fused Pentalenes: Syntheses, Structures, Physical Properties and Applications for Organic Field‐Effect Transistors

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  48. Dibenzopentalenes and Related Compounds

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  49. π‐Extended Pentalenes: The Revival of the Old Compound from New Standpoints

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  50. Deliberate Charge Conjugation Symmetry Breaking for π-Conjugated Electron Acceptor Design

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