Blog

An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties

Chaolumen, Hideto Ito,* Kenichiro Itami*
Chem. Commun.
201955, 9606-9609 . DOI: 10.1039/C9CC03510A
Selected as a front cover in volume 55, issume 65.



[軸不斉π拡張ビアズレンの合成]

近年、ヘリセンのように縮環したキラルなπ共役化合物の合成や物性に興味が持たれている。今回我々は、軸不斉をもつ種々の1,1′-ビアズレン誘導体の合成に成功した。terphenyl基をもつアズレンを出発原料とし、FeCl3で段階的に処理するだけで2,2′-diterphenyl-1,1′-biazuleneとそのπ拡張体を合成した。合成した1,1′-ビアズレン誘導体は軸不斉をもち、キラルカラムでエナンチオマーを容易に分離可能であった。さらに、各種分光学的解析やX線結晶構造解析によってその構造と光物性を明らかにした。

[Axially chiral π-extended biazulenes]

Chiral organic π-conjugated molecules have been intensively investigated in the fields of chiral electronic materials and devices. Herein we report a new motif for an axially chiral 1,1′-biazulene and its π-extended derivative, in which biphenyl was annulated by the electron-rich five-membered-ring of the azulene moiety. These two compounds were unexpectedly synthesized from 2-terphenyl azulene by stepwise intermolecular and intramolecular oxidative C–H/C–H couplings. X-ray diffraction analysis revealed that the crystals of both compounds contain a pair of enantiomers. Furthermore, the axially chiral 1,1′-biazulene derivatives were successfully separated into enantiomers that exhibited clear mirror-image circular dichroism spectra up to the near-infrared region.

Related post

  1. Dragmacidin D Synthesis of Dragmacidin D via D…
  2. Synthesis of Multiply Arylated P…
  3. Synthesis of Sterically Hindered…
  4. Synthesis and Properties of [9]C…
  5. Cyanation of Phenol Derivatives …
  6. Synthesis of Triarylpyridines in…
  7. Synthesis, Properties, and Packi…
  8. Topologically Unique Molecular N…

Twitter@Itami Lab

Itami Lab Facebook

Instagram@Itami Lab

This error message is only visible to WordPress admins

Error: API requests are being delayed. New posts will not be retrieved.

There may be an issue with the Instagram access token that you are using. Your server might also be unable to connect to Instagram at this time.

Error: API requests are being delayed for this account. New posts will not be retrieved.

There may be an issue with the Instagram access token that you are using. Your server might also be unable to connect to Instagram at this time.

Error: No posts found.

Make sure this account has posts available on instagram.com.

Click here to troubleshoot

最近の記事

Flickr@Itamilab

天池先輩からコーヒースープ伴夫妻からのお歳暮です!潤さん、宮村さん、ありがとうございます!!武藤さん、ビールありがとうございます!平賀大都わーいやなさん、あつしさん、ありがとうございます!!だいぶ前だけど、Stripes look #ootdHalloween lookラインを洗う時ですら格好良く。戸谷先生教育実習!imageけいしゅう、誕生日おめでとう!誕生日は英吉家!!3年生に名古屋ぼろ勝ちアピール中!!アリシア卒業おめでとう女子会!
PAGE TOP