Reduced Knoevenagel Reaction of Acetetracenylene-1,2-dione with Acceptor Units for Luminescent Tetracene Derivatives

Abstract

Acetetracenylene-1,2-dione reacted with 3-ethylrhodanine in the presence of piperidine and Hantzsch ester via a Knoevenagel condensation–reduction sequence to give a tetracene–rhodanine adduct. This reduced Knoevenagel product exhibited magenta luminescence with a fluorescence quantum yield of φ = 0.34 and fluorescence lifetime of τ = 13.2 ns in toluene. Electrochemical studies and charge carrier transport measurements revealed ambipolar properties with hole and electron mobilities of 5.1 × 10–7 and 1.6 × 10–4 cm2/(V s), respectively.

Domino Reaction of Aromatic Aldehydes and 1,3-Indanediones for Construction of Bicyclo[2.2.2]octanes and Dibenzo[b,g]indeno[1′,2′:3,4]fluoreno[1,2-d]oxonines

“…The base deprotonation of 1,3-indanedione gave a carbanion ( A ), which in turn condensed with second molecular 1,3-indanedione to give the self-condensated product ( B ). Further condensation with third molecular 1,3-indanedione afforded a trimer ( C ) . The intramolecular aldol condensation gave a cyclized species ( D ), which converted to a hydroxy-substituted cyclohexa-1,3-diene ( E ).…”

“…On the other hand, the easily prepared 2-arylidene-1,3-indanediones are also typical 1,3-dipolarophiles and dienophiles. 2-Arylidene-1,3-indanediones have been widely employed in many Michael addition, condensation reaction, Diels–Alder reaction, cyclization reaction, and domino multicomponent reactions. − In recent years, we have successfully developed several efficient multicomponent reactions for construction of diverse spiroindanones by employing readily available 1,3-indanedione and 2-arylidene-1,3-indanediones as key substrates. , In these research works, we gradually noticed that 1,3-indanedione showed versatile reactivity in multicomponent reactions depending on the reaction conditions …”

Convenient construction of polycyclic architectures via multicomponent reaction of amino acids, dialkyl but-2-ynedioates and 2-(o-hydroxyarylidene)-1,3-indanediones

“…5 Additionally, some indanone-containing polymers have been widely employed in various materials such as nonlinear optical materials, organic photovoltaics and semiconductors. 6 Therefore, many significant synthetic efforts have been devoted to the efficient synthesis of indanone-containing heterocycles. 7,8 For constructing diverse indanone-containing polycyclic systems, the readily available 2-arylidene-1,3-indanediones have been widely employed as the typical 1,3-dipolarophiles and dienophiles in many Michael addition, condensation reaction, Diels–Alder reactions, cyclization reactions and domino multicomponent reactions.…”

Selective Synthesis of Diverse Spiro-oxindole-fluorene Derivatives via a DABCO-Promoted Annulation Reaction of Bindone and 3-Methyleneoxindoles

“…For the synthesis of diverse indanone-containing polycyclic compounds, 1,3-indanediones are useful candidates because they have three contiguous electrophilic and nucleophilic reactive sites in the cyclic 1,3-dicarbonyl scaffold. − More interestingly, the base- or acid-catalyzed self-condensation of 1,3-indanedione afforded the reactive dimer of 1,3-indanedione (bindone) and the cyclotrimer of 1,3-indanedione (truxenone) as well as other oligomers according to the reaction conditions . Both bindone and truxenone are useful scaffolds for various polymer materials such as nonlinear optical, organic photovoltaics, and semiconductors. , On the other hand, the facile base-catalyzed Knoevenagel condensation of 1,3-indanedione with aromatic aldehydes afforded more reactive dipolarophilic 2-arylidene-1,3-indanediones, which were widely employed in many Michael addition, Diels–Alder, annulation, and versatile transformation reactions. − Recently, we successfully found that the triethylamine-promoted reaction of 1,3-indanedione with 3-arylideneindolin-2-ones in ethanol gave carbamato-substituted indeno­[1,2- a ]­fluorenes, in which the bindone was in situ generated and underwent a further domino reaction process . However, the similar triethylamine-mediated reaction of 1,3-indanedione with 3-phenacylideneoxindoles afforded triindanone-fused spiro­[bicyclo[2.2.2]­octane-2,3′-indoline] derivatives, in which a truxenone derivative was initially formed, and sequentially, the [4 + 2] cycloaddition reaction proceeded. , These reactions clearly indicated that 1,3-indanedione and its oligomers showed diverse reactivity in cycloaddition reaction and that various complex polycyclic compounds can be conveniently synthesized by using readily available starting materials .…”