Über Naphthyl‐essigsäuren. (2. Abhandlung): Das Benzphenanthren

Mayer, Fritz; Oppenheimer, Trudi

doi:10.1002/cber.19180510162

Cited by 7 publications

(25 citation statements)

References 3 publications

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“…In this way, several communications from the smallest [5]helicene to the longest [14]carbohelicene were presented. A series of [5]-, 73 [6]-, [7]-, [8]-, [9]-74 [10]-, [11]-, [12]-[13]- 75 and higher helicenes 76 (up to [14]helicene 77 ) were prepared and some fundamental properties of higher carbohelicenes could be determined. Amongst those properties, some high chiroptical values were obtained from circular dichroism spectroscopy and specific rotation measurements.…”

Section: Non-stereoselective Photochemical Syntheses -A Brief Surveymentioning

confidence: 99%

“…It probably came from a rearrangement of [5]helicene. 28 This work was reported just a few weeks before the famous publication of Martin and coworkers describing the first synthesis of [7]helicene 29 (Scheme 4). Those results were important in the history of helicene chemistry.…”

Section: Introduction and Historical Overviewmentioning

confidence: 98%

“…6 It was an early synthesis of a carbohelicene possessing an unambiguous distortion of the p-system. That synthetic procedure was repeated in 1918 7,8 and in 1931. 9,10 The next landmark synthesis was the report of [5]helicene in 1918.…”

Section: Introduction and Historical Overviewmentioning

confidence: 99%

“…A growth of up to 45 annual publications was attained at the beginning of the 21st century. An analysis from Web of knowledge using the search term Scheme 4 Synthesis of [7]helicene by an oxidative photocyclodehydrogenation ).…”

Section: Introduction and Historical Overviewmentioning

confidence: 99%

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One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

2013

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Carbohelicenes belong to a class of fascinating, chiral, and helicoidal molecules, which have a rich history in chemistry since the very beginning of the 20th century. A renewed interest in polyaromatic chemistry and new synthetic challenges toward the search for innovative physical, biological, chemical and opto-electronic properties have brought high motivation in this field of studies. Theoretical insights gained from polyaromatic, chiral, conjugated and distorted π-systems are also responsible for this development. Several synthetic avenues were originally reported for making lower helicenes, but for many years, photochemical synthesis has remained a major method for producing small amount of helicenes. High-dilution conditions is still a limiting factor in their synthesis. The fulgurous impact of organometallic chemistry, novel synthetic methods, and recent catalytic systems has promoted the development of helicene chemistry, toward a library of tailor-made and highly functionalized helicene molecules. Helicene chemistry is being considered as an expanding and modern field, leading to several applications in supramolecular chemistry, in nanosciences, in chemical-biology, in polymers and materials science. This first part of a series of three reviews on carbohelicenes will be devoted to a comprehensive report on non-stereoselective reactions and methods for producing helicenes, along with their functionalization.

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Section: Non-stereoselective Photochemical Syntheses -A Brief Surveymentioning

confidence: 99%

Section: Introduction and Historical Overviewmentioning

confidence: 98%

Section: Introduction and Historical Overviewmentioning

confidence: 99%

Section: Introduction and Historical Overviewmentioning

confidence: 99%

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One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

2013

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“…The carbahelicence are widely synthesized and explored for their electronic and nonlinear optical properties [20][21][22][23][24][25]. The presence of heteroatoms in the helicene backbone significantly alters both the molecular and the self-assembly properties of helical polyaromatics [26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Spectral and optoelectronic studies on 7,12,17-trioxa and 7,12,17-trithia [11] helicenes: a DFT view

Islam

Chimni

2017

Indian J Phys

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Density functional theory has been used to analyse the structural, spectral, charge transport and nonlinear properties of 7,12,17-trioxa [11] helicene and 7,12,17-trithia [11] helicene. The optimised geometries of TOH and TTH shows that carbon-carbon bond lengths of inner fused rings vary from terminal rings, as a consequence of generated torsional strain. The IR-spectra displays characteristics peaks in the region of 750-1550 cm -1 in TOH and a slight shift occurs to lower frequency in case of TTH. The vibrational circular dichroism peaks have major contributions from in and out of plane bending and minor contribution from C=C stretching of fused aromatic rings. From ionisation and reorganization energy values it is evident that TOH and TTH can act as hole transport material for OLED device. As a consequence of extended conjugation in studied system, the higher values of polarizability and hyperpolarizability reflects their role in NLO devices.

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ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

DeTar

2011

Organic Reactions

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In the middle 1890s, three groups of chemists independently discovered a new cyclization reaction of certain appropriately constituted diazonium salts. Fischer and Schmidt reported that an aqueous solution of 2‐benzylbenzenediazonium chloride furnished fluorene on heating. Graebe and Ullman reported that 2‐benzoylbenzenediazonium chloride yielded fluorenone and Staedel reported a somewhat similar result from the action of nitrous acid on 2,2'‐diaminbenozpehnone, a reaction that produced a little 1‐hydroxyfluorenone. Two years later, Robert Pschorr applied the ring closure reaction to the diazonium salt derived from trans‐2‐amino‐alpha‐phenylcinnamic acid to obtain phenanthrene‐9‐carboxylic acid. The principal utility of these cyclizations reactions has been the synthesis of substituted ring structures in which the positions of the substituents are known.

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Über Naphthyl‐essigsäuren. (2. Abhandlung): Das Benzphenanthren

Cited by 7 publications

References 3 publications

One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes

Spectral and optoelectronic studies on 7,12,17-trioxa and 7,12,17-trithia [11] helicenes: a DFT view

ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

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