DOUBLE FJORD MOTIF IN OVERCROWDED LARGE POLYCYCLIC AROMATIC HYDROCARBONS: THE CONFORMATIONAL SPACE OF HEXABENZO[a,cd,f,j,lm,o]PERYLENE

Marom, Hili; Pogodin, Sergey; Agranat, Israel

doi:10.1080/10406630701481049

Cited by 17 publications

(27 citation statements)

References 34 publications

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“…In agreement with this, X-ray crystallographic analysisr evealed the C 5 -symmetricalp ropeller-shaped structures, which weree ssentially the same as those of the DFT-calculated stereoisomers )). An experimental kinetic study on the basis of a temperature-dependent decrease in the ee of 18 in solution, as monitored by HPLC disclosed ar acemization barrier of 143 kJ mol À1 at 298 K, which was in good agreement with the DFT-calculated value (144 kJ mol À1 )a nd slightly lower than that of [6]helicene. [12] Multiple heterohelicenes contain at least one heteroatomi n the multiply helical skeleton, on the basis of the definition of heterohelicenes, [1b, e] which, however,d oes not stipulate the aromaticity of the heterocycles.…”

Section: As Urvey Of Structuressupporting

confidence: 72%

“…The first documented double [6]helicene was 4 ( Figure 1), which was first synthesized by Laarhoven and Cuppen in 1973. [10] From the product mixture obtained through photocyclization of 2,6-bis[2-(3'-phenanthryl)ethenyl]naphthalene, two isomerso f4 were isolated.…”

Section: As Urvey Of Structuresmentioning

confidence: 99%

“…Unfortunately,t he crystal structure of 4 was not reported. In 2015, Itami and co-workers synthesized a p-extended double [6]helicene, 5 (Figure 1 Chem. Asian J.…”

Section: As Urvey Of Structuresmentioning

confidence: 99%

“…DFT calculations indicated that twisted-5 was thermodynamically more stable than that of meso-5 by 3.8 kJ mol À1 ,w hichs uggested that the as-synthesized isomeric mixture of 5 did not reach equilibrium. The energy barrierf or the twisted-to-meso interconversion was calculated to be 182 kJ mol À1 ,w hich was considerably highert han that of [6]helicene (156 kJ mol À1 ), [12] and comparable with that of [7]helicene (174 kJ mol À1 ). [1b] Narita and co-workers synthesized double [ 7]helicenes 6 (Figure 1) through the Scholl reaction, which exhibited good regioselectivity,a sd iscussed in the next section.…”

Section: As Urvey Of Structuresmentioning

confidence: 99%

“…Very recently,I tami and co-workers reported quintuple [6]helicene 18,w hich was the first example of ap olycyclic aromatic hydrocarbon containing five [6]helicenes in af used p system. [29] Containing ac orannulene core, compound 18 was synthesized from corannulene in three steps, including af ivefold intramolecular direct arylation.…”

Section: As Urvey Of Structuresmentioning

confidence: 99%

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Recent Progress in Chemistry of Multiple Helicenes

Yong

Miao

2018

Chemistry An Asian Journal

211

106

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The last decade has witnessed multiple helicenes arising as an interesting class of nonplanar polycyclic aromatics of inherent multihelicity. These molecules present esthetic structures and interesting properties not available to helicenes of single helicity. Herein an overview of multiple helicenes with respect to structures, stereochemical dynamics, synthesis, and applications is provided. Recently reported multiple helicenes are surveyed with an emphasis on molecular structures and stereochemistry of multiple carbohelicenes. After this survey, the synthesis of multiple helicenes through the Scholl reaction is discussed and recent applications of multiple helicenes in organic electronics are summarized. On the basis of these discussions, conclusions are reached on the current status of multiple helicenes and an outlook for this field is provided.

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Section: As Urvey Of Structuressupporting

confidence: 72%

Section: As Urvey Of Structuresmentioning

confidence: 99%

“…Unfortunately,t he crystal structure of 4 was not reported. In 2015, Itami and co-workers synthesized a p-extended double [6]helicene, 5 (Figure 1 Chem. Asian J.…”

Section: As Urvey Of Structuresmentioning

confidence: 99%

Section: As Urvey Of Structuresmentioning

confidence: 99%

Section: As Urvey Of Structuresmentioning

confidence: 99%

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Recent Progress in Chemistry of Multiple Helicenes

Yong

Miao

2018

Chemistry An Asian Journal

211

106

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Enantioselective Synthesis of 1,12‐Disubstituted [4]Helicenes

et al. 2020

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A highly enantioselective synthesis of 1,12‐disubstituted [4]carbohelicenes is reported. The key step for the developed synthetic route is a Au‐catalyzed intramolecular alkyne hydroarylation, which is achieved with good to excellent regio‐ and enantioselectivity by employing TADDOL‐derived (TADDOL=α,α,α,α‐tetraaryl‐1,3‐dioxolane‐4,5‐dimethanol) α‐cationic phosphonites as ancillary ligands. Moreover, an appropriate design of the substrate makes the assembly of [4]helicenes of different substitution patterns possible, thus demonstrating the synthetic utility of the method. The absolute stereochemistry of the newly prepared structures was determined by X‐ray crystallography and characterization of their photophysical properties is also reported.

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