Synthesis, resolution and racemization study of helically twisted o-terphenyls

Gao, Jianmei; Meng, Xian Sheng; Bender, Timothy P.; MacKinnon, Sean M.; Grand, Valerie; Wang, Zhi Yuan

doi:10.1039/a901474h

Cited by 18 publications

(9 citation statements)

References 13 publications

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“…We will mainly report Several chiral [5]helicene derivatives (partly saturated or not) containing an anhydride or an imide function were common monomers found in the literature, and their synthesis was reported. 119 Those helicene-based polymers have been investigated since the mid 1990's as almost exclusively polyimides. 120 In 1995, a high-temperature polyimides polymer based on thermal polymerization of several diamines with [5]helicene-5,6,9,10-tetracarboxylic 5,6,9,10-dianhydride was reported.…”

Section: Helicene-based Polymers and Copolymersmentioning

confidence: 99%

One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

2013

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Carbohelicenes are a class of fascinating chiral helical molecules which have a rich history in chemistry. Over a period of almost 100 years, chemists have developed many methods to prepare them in a racemic or in a non-racemic form. They also possess a series of interesting chiral, physical, electronic and optical properties. However, their utilization in chemistry or chemistry-related fields has rarely appeared in a detailed and comprehensive review. It is the purpose of this review to collect fundamental applications and functions involving carbohelicenes in various disciplines such as in materials science, in nanoscience, in biological chemistry and in supramolecular chemistry. From the numerous synthetic methodologies reported up to now, carbohelicenes and their derivatives can be tailor-made for a better involvement in several subfields. Among those domains are: nanosciences, chemosensing, liquid crystals, molecular switches, polymers, foldamers, supramolecular materials, molecular recognition, conductive and opto-electronic materials, nonlinear optics, chirality studies and asymmetric synthesis. Helicene chemistry is now at a developmental stage, where sufficient application data are now collected and are extremely useful. They provide many more ideas for setting up the basis for future innovative applications.

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Section: Helicene-based Polymers and Copolymersmentioning

confidence: 99%

One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

2013

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“…Helical conjugated structures offer diverse fascinated features such as a higher highest occupied molecular orbital–lowest unoccupied molecular orbital gap compared to the corresponding linear poly aromatic hydrocarbons because of weak delocalization caused by the twisted geometry, formation of complexes with metals, enhanced optical rotations and chiroptical properties, and through space interactions. , Thus, it is not surprising that molecules with helical spatial architecture such as helicenes and helicenoids attract considerable attention in modern chemical science. Furthermore, their twisted geometry resembling natural biopolymers is an additional alluring factor.…”

Section: Introductionmentioning

confidence: 99%

Directional Approach to Enantiomerically Enriched Functionalized [7]Oxa-helicenoids and Groove-Based Selective Cyanide Sensing

et al. 2019

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Several regioselective functionalized mono-and disubstituted [7]oxa-helicenoids have been synthesized in the enantiomerically enriched (90−99% ee) form. These functionalized helicenoids exhibited pronounced spectral and chiroptical properties suitable for sensing applications. In particular, corresponding helicenoid's mono and dialdehydes have been effectively used as chemodosimeters for selective detection of cyanide anions over other anions, while simple aromatic aldehydes do not function as cyanide sensors. The groove available in the helical host plays a crucial role in the sensing. The enantiomerically enriched nature of the sensors allows the use of electronic circular dichroism as an uncommon detection tool for cyanide anions, along with conventional fluorescence and NMR methods.

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“…Chiral helical structures are widely seen in the living systems as represented by the helical motifs of DNA duplex and α -helix in peptides and have been attracting much attention because such well-defined structures often inspire us to utilize the scaffold for various applications such as stereoselective reactions, optical resolution, molecular recognition, and molecular sensory and memory systems. In this context, much effort has been directed toward constructing chiral helical molecules such as helicenes, metallohelicates, and screw-shaped polymers …”

Section: Introductionmentioning

confidence: 99%

Solvent Effect on Helicity Induction of Zinc Bilinone Bearing a Chiral Auxiliary at the Helix Terminal

et al. 2001

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Solvent effects on helicity induction in zinc bilinone (ZnBL) derivatives bearing chiral auxiliaries at their 19-positions were investigated by using circular dichroic spectroscopy and (1)H NMR experiments. In ZnBLs 1 and 2, which possess (R)-2-methyl-1-phenylpropyloxy and (R)-1-phenylethyloxy groups at their 19-positions, respectively, the efficiency of helicity induction was significantly affected by employed solvents (78-95% de in 1 and 33-89% de in 2). The free energy changes of the P-M interconversion of 1 and 2 were linearly in proportion to reduction in polarizability of solvents: lower polarizability of solvents led to better efficiency of helicity induction in 1 and 2. With the support of the (1)H NMR study in addition to the molecular modeling previously reported, it was indicated that the solvophobic van der Waals interaction between the alkyl group in the chiral auxiliary and the A-ring of the bilinone skeleton in the preferred conformer plays a crucial role in determining the efficiency of helicity induction in 1 and 2.

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Synthesis, resolution and racemization study of helically twisted o-terphenyls

Abstract: The synthesis, resolution and racemization studies of helical o-terphenyls, useful chiral building blocks are reported.

Cited by 18 publications

References 13 publications

One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

One hundred years of helicene chemistry. Part 3: applications and properties of carbohelicenes

Directional Approach to Enantiomerically Enriched Functionalized [7]Oxa-helicenoids and Groove-Based Selective Cyanide Sensing

Solvent Effect on Helicity Induction of Zinc Bilinone Bearing a Chiral Auxiliary at the Helix Terminal

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