Aryne‐Based Synthesis of Cyclobutadiene‐Containing Oligoacenes and Related Extended Biphenylene Derivatives

to related objects

Abstract: A previously undescribed aryne derived from a π‐extended biphenylene, 2,3‐didehydrobenzo[b]biphenylene, has been developed. The participation of this new aryne building block in [4+2] and palladium‐catalyzed [2+2+2] cycloaddition reactions has been applied to the synthesis of a variety of polycyclic conjugated hydrocarbons (PCHs) with appealing structures which combine (aromatic) benzene and (antiaromatic) cyclobutadiene (CBD) rings. Among them, a family of unsubstituted (or barely substituted) CBD‐oligoacenes has been accessed by iterative Diels‐Alder reactions of the new aryne with furans and/or isobenzofurans, followed by deoxygenative aromatization of the resulting epoxy‐derivatives. The experimental and computational studies of the newly synthesized PCHs suggest an important degree of electron delocalization along the polycyclic skeleton, more pronounced in the linearly fused derivatives. The computed ACID plots reveal clockwise current density vectors at the peripheral bonds, originating from the σ contributions of the antiaromatic cyclobutadiene rings.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Aryne‐Based Synthesis of Cyclobutadiene‐Containing Oligoacenes and Related Extended Biphenylene Derivatives ; day:02 ; month:02 ; year:2024 ; extent:10
Advanced synthesis & catalysis ; (02.02.2024) (gesamt 10)

Creator: Álvarez, Berta
Janeiro, Jesús
Cobas, Agustín
Ortuño, Manuel A.
Peña, Diego
Guitián, Enrique
Pérez, Dolores

DOI: 10.1002/adsc.202301264

URN: urn:nbn:de:101:1-2024020314123253192852

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:36 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Álvarez, Berta
Janeiro, Jesús
Cobas, Agustín
Ortuño, Manuel A.
Peña, Diego
Guitián, Enrique
Pérez, Dolores

Other Objects (12)

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Hochschulschrift

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Hochschulschrift

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Hochschulschrift

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.

Aryne‐Based Synthesis of Cyclobutadiene‐Containing Oligoacenes and Related Extended Biphenylene Derivatives

Object Details

References and Relationships

Contributors, Places and Time

Further information

Data provider

Associated

Other Objects (12)

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

π-Extended quinolinioum derivatives: synthesis, properties, classification

Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine

Synthesis of Selenium-Containing Chitosan Derivatives and Their Antibacterial Activity

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Stereoselective synthesis of P7C3 class derivatives and related fluoroorganics

Tetraphenylmethane Derivatives Containing Nitrogen Heterocycles

Synthesis and antifungal activity of novel pyrazolecarboxamide derivatives containing a hydrazone moiety

Microwave synthesis and thermal properties of polyacrylate derivatives containing itaconic anhydride moieties

Design, Synthesis, and Evaluation of Benzoheterocyclic-Containing Derivatives as Novel HDAC1 Inhibitors

Synthesis and Characterization of Palladium-Containing Polyoxometalates and Polyoxometalate-Based Extended Networks

Synthesis and antibacterial activity of novel levofloxacin derivatives containing a substituted thienylethyl moiety

Design, synthesis, and antiviral activities evaluation of novel quinazoline derivatives containing sulfonamide moiety

Related objects

Reset password