Concave Butterfly-Shaped Organometallic Hydrocarbons?

Laskoski, Matthew; Roidl, Gaby; Smith, Mark D.; Bunz, Uwe H. F.

doi:10.1002/1521-3773(20010417)40:8<1460::aid-anie1460>3.0.co;2-q

Cited by 38 publications

(13 citation statements)

References 30 publications

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“…Known ferrocenyl-acetylenes have been shown to have considerable potential in NLO, catalysis, as models of charge transfer and in the synthesis of more complex molecules with well-defined magnetic and electronic properties. 4,[11][12][13] Given these considerations, 13 became a desirable target molecule (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterisation of novel ferrocenyl polyphenylenes

et al. 2012

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This work describes the synthesis and characterisation of a new series of polyphenylenes with up to four ferrocenyl moieties. The synthetic route involves the preparation of a number of novel precursors. Cyclopentadienones, generated from the two-fold Knoevenagel condensation of di-ferrocenyl propanones and diketones, are used in [2 + 4] Diels-Alder cycloadditions with appropriately substituted acetylenes. 13 is amongst the compounds isolated. It is the largest ferrocenyl-supported polyaromatic hydrocarbon (PAH) to date. Prepared via a Sonogashira cross-coupling reaction between ethynyl-Fc and iodo-HBC, it comprises a hexa-peri-hexabenzocoronene (HBC) core linked via acetylene to a ferrocenyl unit (Fc). The electrochemical and absorption properties of the ferrocenyl-polyphenylenes and the fully conjugated 13 are discussed. The NLO data for 13, determined by hyper Rayleigh scattering techniques, are compared to those of similar fulleryl-based compounds in the literature.

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Section: Introductionmentioning

confidence: 99%

The synthesis and characterisation of novel ferrocenyl polyphenylenes

et al. 2012

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“…1 H NMR measurements revealed that cyclobutadienyl moieties in 217 and 218 and cyclopentadienyl moieties in 219 and 220 are more aromatic than the benzene ring in 89 a according to the ring‐current criterion. π‐Expanded macrocycles 221 – 224 containing cobalt and iron complexes were synthesized . Because of the square‐shaped cyclobutadienyl ligand, cobalt complexes 221 (CCDC: 154093), 222 (CCDC: 176513), and 224 (CCDC: 176515) containing π‐expanded cyclobutadienyl ligands are strain free.…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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“…The concave butterfly-shaped organometallic hydrocarbon 80 has been synthesized stating from a 1,2,3,4-tetraethynylcyclobutadiene complex using Pd-catalysed cross-coupling and cyclization methodology. 111 Employing similar methodology, ferrocene-fused 81 and benzo [14]annulene 82 have been synthesized. 112 From comparison of 1 H NMR data it was found that a benzene ring disturbs the aromaticity of the fused dehydro [14]annulene less than a ferrocene ring and that there is a stronger localization of the dehydro [14]annulene than for benzo-fused 82.…”

Section: Nonbenzenoid Aromaticsmentioning

confidence: 99%