Chiral Carbon‐rich Macrocycles and Cyclophanes

Campbell, Katie; Tykwinski, Rik R.

doi:10.1002/3527607994.ch6

Cited by 20 publications

(12 citation statements)

References 72 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2 was synthesized similarly to 1 (Scheme 4), whereas a different synthetic route for 3 was employed (Scheme 5) (see footnote 3 ). For the synthesis of 3, an amide 7 obtained according to the literature 97 was converted into the corresponding aniline 8 under an alkaline condition.…”

Section: Designs and Syntheses Of 2 Andmentioning

confidence: 99%

“…1C). [10][11][12][13][14][20][21][22][23][24][25][26][27][28][29][30][31] Bridging between P and Q with two flexible linkers (L 1 s) generates cyclic molecules such as cyclophanes [1][2][3][4][5][6][7][8][9][15][16][17][18][19] and strapped porphyrins, [50][51][52][53][54][55][56] which is also one of the most widely used strategy (Fig. 1D).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Isocyanurates with Planar Chirality: Design, Optical Resolution, and Isomerization

et al. 2012

View full text Add to dashboard Cite

Designs and syntheses of isocyanurates (1-3) are described on the basis of a novel concept that two enantiotopic faces of C(s) -symmetric, prochiral planar molecules are differentiated with a location of groups at the top or bottom of the planar skeleton using a rigid linker. Such isocyanurates are atropisomeric. The planar-chiral structures of 1 and 2(anti) (anti-conformer of 2) were confirmed by single-crystal X-ray analyses, and the space groups were P1 (for 1) and P2(1)/c (for 2(anti)), resulting that the crystals were racemates. Optical resolutions of 1-3 were successfully accomplished by using chiral high-performance liquid chromatography technique in combination with circular dichroism, absorption, and nuclear magnetic resonance spectroscopies and mass spectrometry. Furthermore, the rotational barriers (ΔG(‡)s) related to isomerizations of 1-3 were estimated to be 27.2 (for 1 at 50 °C), 27.6 (for 2(anti) at 50 °C), and 40.6 (for 3(syn) at 150 °C) kcal/mol. The ΔG(‡)s of 2 and 3 were higher than that of 1 and, in particular, that of 3 was highest among them. This result indicates that an introduction of bulky substituents and an intramolecular bridging are effective for inhibitions of the isomerizations.

show abstract

Section: Designs and Syntheses Of 2 Andmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isocyanurates with Planar Chirality: Design, Optical Resolution, and Isomerization

et al. 2012

View full text Add to dashboard Cite

show abstract

“…Building upon these purely aromatic helically chiral structures, in 1972 Staab and coworkers68 prepared a carbon-rich helically chiral benzannulene structure composed solely of benzene and acetylene moieties. Since that time a rich chemistry of chiral benzannulene compounds has been developed 69. Similarly, chirality can be introduced into carbon-rich systems through the incorporation of chiral moieties, such as binaphthyl units.…”

Section: Novel Stereoisomeric Supramolecular Trianglesmentioning

confidence: 99%

Carbon-rich supramolecular metallacycles and metallacages

2008

View full text Add to dashboard Cite

Coordination-driven self-assembly via the directional-bonding approach utilizes rigid transition metal acceptors and electron-rich donors to allow for complex, nanoscale 2D polygons and 3D polyhedra to be prepared under mild conditions and in high yields. To ensure proper rigidity and directionality, many acceptor and donor precursors contain largely carbon-rich aromatic and/or acetylenic moieties. This article introduces self-assembly as an alternative means of synthesizing carbon-rich materials and discusses the development, design, synthesis, and applications of carbon-rich supramolecular metallacycles and metallacages as well as the self-assembly of new diastereomeric carbon-rich supramolecular triangles.

show abstract

“…SPMs allow the incorporation of functional side groups at defined positions, strongly influencing the properties and applications of these compounds. Chiral SPMs are of great interest because their unique structures provide potential utilities for sensing, guest recognition, separation, as well as ligands for asymmetric catalysis …”

Section: Introductionmentioning

confidence: 99%

“…Chiral SPMs are of great interest because their unique structures provide potential utilities for sensing, guest recognition, separation, as well as ligands for asymmetric catalysis. 16,18,[20][21][22] We have chosen allenes as our chiral motif and, in particular, diethynylallene (DEA) 1 23,24 (Fig. 2) to build macrocyclic systems with 3D-topologies in a simple way.…”

Section: Introductionmentioning

confidence: 99%

Conformational Stable Alleno‐Acetylenic Cyclophanes Bearing Chiral Axes

et al. 2014

View full text Add to dashboard Cite

The design and synthesis of chiral cyclophanes containing signaling functional groups as an integral part of the macrocyclic framework offer promising possibilities for chiral sensing, molecular recognition, and chiral supramolecular architectures. Our research group has been involved in the construction and study of chiroptical properties of several allenic meta- and para-cyclophanes bearing anthracene and pyridine rings as spacers. A revision of our results is presented.

show abstract

Chiral Carbon‐rich Macrocycles and Cyclophanes

Cited by 20 publications

References 72 publications

Isocyanurates with Planar Chirality: Design, Optical Resolution, and Isomerization

Isocyanurates with Planar Chirality: Design, Optical Resolution, and Isomerization

Carbon-rich supramolecular metallacycles and metallacages

Conformational Stable Alleno‐Acetylenic Cyclophanes Bearing Chiral Axes

Contact Info

Product

Resources

About