Site‐Selective Sonogashira Reactions of 1,4‐Dibromo‐2‐fluorobenzene – Synthesis and Properties of Fluorinated Alkynylbenzenes

Reimann, Stefan; Sharif, Muhammad; Hein, Martin; Villinger, Alexander; Wittler, Kai; Ludwig, Ralf; Langer, Peter

doi:10.1002/ejoc.201100394

Cited by 11 publications

(4 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although site-selective Sonogashira reactions of 1,4-dibromo-2-fluorobenzene with 4-alkylbenzene acetylene was reported by Reimann [27] with satisfied yield of 80%, an inevitable dimer by-product appeared which is difficult to be isolated. In our work, fluoro derivatives of 1-iodo-4-bromobenzene were used as starting materials and a higher selectivity and yield were obtained.…”

Section: Resultsmentioning

confidence: 97%

The effect of lateral fluorination on the properties of phenyl-tolane liquid crystals

Li¹,

Yang²,

Gan³

et al. 2015

Liquid Crystals

View full text Add to dashboard Cite

Multifluorinated phenyl-tolane liquid crystals were synthesised by two steps cross-coupling reactions, and their structures were confirmed by nuclear magnetic resonance (NMR), mass spectra (MS) and infrared spectrometry (IR). All of these compounds show only nematic phase, and their melting points decrease dramatically with the introduction of lateral fluorine atom. The physical properties of the compounds were also evaluated. The extrapolated birefringence of the compounds are at the range of 0.32-0.37 at 589 nm, and the dielectric anisotropies exist between 3.1 and 20.6, and the rotational viscosities are as low as 63.7-130.7 mPa·s. With the increase of lateral fluorine substituents in the benzene ring, the Δε value increases tremendously while the clearing points, birefringence and rotational viscosity decrease. These compounds show good solubilities and are favourable to form eutectic mixtures. The effect of lateral fluorine atoms at different region of the core on the dielectric anisotropy and mesophase is also discussed.

show abstract

Section: Resultsmentioning

confidence: 97%

The effect of lateral fluorination on the properties of phenyl-tolane liquid crystals

Li¹,

Yang²,

Gan³

et al. 2015

Liquid Crystals

View full text Add to dashboard Cite

show abstract

“…It is observed that the absorbance maxima for 43 (λ max =321–331 nm) is higher than that of 42 (λ max =285–318 nm) [79] . This is attributable to the greater extended π‐conjugation in the former (Figure 1).…”

Section: Photophysical Properties Of Pahsmentioning

confidence: 93%

“…It is observed that the absorbance maxima for 43 (λ max = 321-331 nm) is higher than that of 42 (λ max = 285-318 nm). [79] This is attributable to the greater extended π-conjugation in the former (Figure 1). The compounds 42 e-f and 43 e-f containing tert-butyl and methoxy groups show redshift in absorption maxima when compared to 42 a and 43 a.…”

Section: Minireviewmentioning

confidence: 99%

“…In 2012, Langer reported the selective coupling of bromo substituents with aryl alkynes in the presence of fluoro groups on the aryl ring (Scheme 13) to obtain fluorinated alkynylbenzenes with moderate to good yields (Scheme 13). [79] The bromo group present adjacent to fluorine in 41 , is less likely to undergo the first alkynyl substitution due to steric hindrance and high electron density (equation 1, Scheme 13). However upon use of excess aryl alkyne 5 , the bromo group adjacent to fluorine in 41 could be substituted by the alkynyl group (equation 2, Scheme 13).…”

Section: Synthesis Of Polyethynyl Containing Pahs By Multi‐fold Sonogashira Reactionmentioning

confidence: 99%

See 1 more Smart Citation

Polycyclic Aromatic Hydrocarbons Bearing Polyethynyl Bridges: Synthesis, Photophysical Properties, and their Applications

2021

View full text Add to dashboard Cite

Polyacetylene bridged π-conjugated polyaromatic hydrocarbons (PAHs) have found wide applications in the fabrication of organic field-effect transistors (OFETs), organic light emitting diodes (OLEDs), solar cells, organic photovoltaic devices (OPV), liquid crystal displays and sensors. The ease with which semiconducting and/or emissive behaviour of polyacetylene bridged PAHs could be modulated by tailored functionalities via state-of-art powerful synthetic tools along with their low production cost and mechanical flexibility makes them one among the favourites for versatile optoelectronic and sensing applications. The current review sheds light on the applicability of Sonogashira coupling in the synthesis of PAHs with alkynyl bridges with particular emphasis on their photophysical properties. The review further discusses the utility of alkynyl bridged PAHs from the point of view of their applications in optoelectronic devices and in sensing nitroaromatics. The rich synthetic Sonogashira coupling that is available at one's disposal along with the promising photophysical properties demonstrated by alkynyl bridged PAHs offers great promise in design of novel πconjugated molecules that are capable of exhibiting exciting optoelectronic and sensing applications.

show abstract

ChemInform Abstract: Site‐Selective Sonogashira Reactions of 1,4‐Dibromo‐2‐fluorobenzene — Synthesis and Properties of Fluorinated Alkynylbenzenes.

Reimann¹,

Sharif²,

Hein³

et al. 2012

ChemInform

View full text Add to dashboard Cite

show abstract

Site‐Selective Sonogashira Reactions of 1,4‐Dibromo‐2‐fluorobenzene – Synthesis and Properties of Fluorinated Alkynylbenzenes

Cited by 11 publications

References 38 publications

The effect of lateral fluorination on the properties of phenyl-tolane liquid crystals

The effect of lateral fluorination on the properties of phenyl-tolane liquid crystals

Polycyclic Aromatic Hydrocarbons Bearing Polyethynyl Bridges: Synthesis, Photophysical Properties, and their Applications

ChemInform Abstract: Site‐Selective Sonogashira Reactions of 1,4‐Dibromo‐2‐fluorobenzene — Synthesis and Properties of Fluorinated Alkynylbenzenes.

Contact Info

Product

Resources

About