5,10,15-Trimethylenetribenzo[a,f,k]trindene (Truxenene)

Sbrogiò, Federico; Fabris, Fabrizio; Lucchi, Ottorino De; Lucchini, Vittorio

doi:10.1055/s-1994-23001

Cited by 19 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We ascribe these observations to a polymerization reaction involving the vinyl group of vtt. Reports on polymerization reactions for truxenene (a close relative of the H 3 vtt ligand) are not available in the literature. However, truxenene can be considered as a derivative of dibenzofulvene, and researchers have demonstrated that dibenzofulvene can polymerize with cationic, anionic, and radical initiators .…”

Section: Resultsmentioning

confidence: 99%

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Alkaş

Friche

Harris

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

Methods to synthesize and characterize aromatic molecules with vinyl substituents are sought after yet limited in the literature. Here, we introduce cyclobutyl groups into a metal–organic framework (MOF) matrix that are poised to produce ethylene upon heating. The expulsion of ethylene produces vinyl groups on an aromatic core, which are isolated by the crystalline matrix of the framework. This enables full characterization of the thermolysis by single‐crystal X‐ray diffraction. Further, we modify the vinyl groups by a bromine addition reaction. Importantly, the two transformations happen in a single‐crystal‐to‐single‐crystal manner without changing the overall network structure of the parent framework. New insights into the structural and synthetic chemistry of this important class of compound are generated. Installing reactive vinyl tags in materials by the high temperature thermolysis of cyclobutyl groups is a powerful strategy for altering their physicochemical characteristics.

show abstract

Section: Resultsmentioning

confidence: 99%

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Alkaş

Friche

Harris

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Truxenone, 86, was originally prepared directly via the acid-catalysed triple condensation of indane-1,3-dione [72,73], but the more recent five-step synthesis starting from 2methylacetophenone (Scheme 26) proceeds under milder conditions and is more tolerant to sensitive substituents [74].…”

Section: Applications Of Truxene and Truxenonementioning

confidence: 99%

Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry

Lock,

Reginato,

Bruno-Colmenárez

et al. 2023

Molecules

View full text Add to dashboard Cite

The triple condensation of cyclopentanone or indanone to trindane (C15H18) or truxene (C27H18), respectively, provides convenient access to molecular skeletons on which major fragments of the prototypical fullerene C60 can be assembled. In particular, early approaches (both organic and organometallic) towards sumanene, as well as the final successful synthesis, are described. Organometallic derivatives of trindane have been prepared in which Cr(CO)3, Mo(CO)3, [Mn(CO)3]+ or [(C5H5)Fe(CO)2]+ are η6-bonded to the central arene ring. The debromination of hexabromotrindane yields trindene, which forms a tri-anion to which as many as three organometallic fragments, such as Mn(CO)3, W(CO)3Me, or Rh(CO)2, may be attached. Truxene forms complexes whereby three metal fragments can bind either to the peripheral arene rings, or to the five-membered rings, and these can be interconverted via η6 ↔ η5 haptotropic shifts. Truxene also forms a double-decker sandwich with Ag(I) bridges, and decacyclene, C36H18, forms triple-decker sandwiches bearing multiple cyclopentadienyl-nickel or -iron moieties. The organic chemistry of trindane has been investigated, especially with respect to its unexpectedly complex oxidation products, which were only identified unambiguously via X-ray crystallography. The three-fold symmetric trindane framework has also been used as a template upon which a potential artificial receptor has been constructed. Finally, the use of truxene and truxenone derivatives in a wide range of applications is highlighted.

show abstract

“…14 This heptacyclic polyarene has been recognized as a potential starting material for the construction of large polyarenes by several groups 15. 16, 17, 18 Two alternative preparations of 2 have been reported. The first, reported by Jennenskens et al,19 was based on the dehydrogenation of polyarenes in the presence of S 8 , which gave predominantly the C 1 isomer of 2 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of C₃ Benzo[1,2‐e:3,4‐e′:5,6‐e′′]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium‐Catalyzed Arylation

Gómez‐Lor

Cantalapiedra

Ruíz

et al. 2004

Chemistry A European J

View full text Add to dashboard Cite

show abstract

5,10,15-Trimethylenetribenzo[a,f,k]trindene (Truxenene)

Cited by 19 publications

References 0 publications

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry

Synthesis of C₃ Benzo[1,2‐e:3,4‐e′:5,6‐e′′]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium‐Catalyzed Arylation

Contact Info

Product

Resources

About

5,10,15-Trimethylenetribenzo[a,f,k]trindene (Truxenene)

Cited by 19 publications

References 0 publications

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Thermal Elimination of Ethylene from Cyclobutyl Groups Characterized by X‐ray Crystallography in a Metal–Organic Framework Matrix

Syntheses, Structures and Reactivity of Metal Complexes of Trindane, Trindene, Truxene, Decacyclene and Related Ring Systems: Manifestations of Three-Fold Symmetry

Synthesis of C3 Benzo[1,2‐e:3,4‐e′:5,6‐e′′]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium‐Catalyzed Arylation

Contact Info

Product

Resources

About

Synthesis of C₃ Benzo[1,2‐e:3,4‐e′:5,6‐e′′]tribenzo[l]acephenanthrylenes (“Crushed Fullerene” Derivatives) by Intramolecular Palladium‐Catalyzed Arylation