Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene

CHEN Jian; DU Wei-song; GAO Chao

doi:null

您当前的位置：

首页 >

文章列表页 >

Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene

更新时间：2020-08-12

- Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene
- Chinese Journal of Liquid Crystals and Displays Vol. 29, Issue 4, Pages: 508-514(2014)
- 作者机构：
  
  西安近代化学研究所,陕西西安,710065
- 作者简介：
- 基金信息：
- DOI：
  CLC：
- Received：29 December 2013，
  
  Revised：15 January 2014，
  
  Published：05 August 2014
- 稿件说明：
移动端阅览
陈键, 杜渭松, 高潮. 六（十二烷基）六苯并蒄的简便合成[J]. 液晶与显示, 2014,29(4): 508-514

CHEN Jian, DU Wei-song, GAO Chao. Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene[J]. , 2014,29(4): 508-514
陈键, 杜渭松, 高潮. 六（十二烷基）六苯并蒄的简便合成[J]. 液晶与显示, 2014,29(4): 508-514 DOI：

CHEN Jian, DU Wei-song, GAO Chao. Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene[J]. , 2014,29(4): 508-514 DOI：

摘要

为了提高六（十二烷基）六苯并蒄的收率，设计了一条新合成路线。该方法首先以二苯乙炔为初始原料，经过环化三聚和碘代得到六（4-碘苯基）苯，该中间体在钯催化下与1-溴代十二烷发生Kumada交叉偶联，最后环化氧化脱氢制得目标产物。借助于

HNMR和元素分析手段表明产物是目标化合物，并对该材料的光学性能、热学性能以及电化学性能进行了研究。该路线使目标物的总收率由27%提高到40.9%。与文献提供的方法相比，新法具有合成步骤少、纯化难度低、成本低廉等优点。

Abstract

In order to improve the yield of hexakis(4-dodecy)-peri-hexabenzocoronene

a new synthetic approach is designed. First

hexa(4-iodophenyl)benzene is synthesized by cyclotrimerization of diphenylacetylene and then iodosubstitued. A palladium catalyzed Kumada cross-coupling reaction of 1-Bromododecane with that intermedium and cyclodehydrogenation are utilized in the last two reaction steps. The chemical structure of the target compound is characterized by

H NMR and elemental ana-lysis

and the optical

thermal and electrochemical properties of this HBC material are studied. The yield is improved to 40.9%

which showed 13% higher than that of the general method. This novel synthetic routine has advantages of simpler purification

fewer reaction steps and lower costing over that reported in the article before.

关键词

Keywords

references

陈树森,李田,赵达慧.盘状液晶材料的研究进展[J]. 物理化学学报,2010,26(4): 1124-1134. Chen S S, Li T, Zhao D H. Progress in discotic liquid crystalline materials [J]. Acta Physico Chimica Sinica, 2010, 26(4): 1124-1134. (in Chinese)[2] Kumar S. Self-organization of disc-like molecules: chemical aspects [J]. Chem. Soc. Rev., 2006, 35 (1): 83-86.[3] Bisoyi H K, Kumar S. Discotic nematic liquid crystals: science and technology [J]. Chem. Soc. Rev. , 2010, 39 (1): 264-285.[4] 崔晓鹏, 王磊, 黄琪, 等. 基于异烟酸酯类衍生物的超分子盘状液晶构建[J]. 液晶与显示,2011,26(6): 727-732. Cui X P, Wang L, Huang Q, et al. Supramolecular discotic liquid crystals formed by hydrogen bonding of isonicotinic acid derivatives [J]. Chinese Journal of Liquid Crystals and Displays, 2011, 26(6): 727-732. (in Chinese)[5] Lukas F D, Valentin K, Ian A H, et al.Synthesis and controlled self-assembly of covalently linked Hexa-peri-hexabenzocoronene/Perylene Diimide dyads as models to study fundamental energy and electron transfer processes [J]. J. Am. Chem. Soc., 2012, 134:5876-5886.[6] O'Neill M, Kelly S M. Liquid crystals for charge transport, luminescence, and photonics [J]. Adv. Mater., 2003, 15: 1135-1146.[7] van de Craats A M, Warman J M, Fechtenkotter A, et al. Record charge carrier mobility in a room-temperature discotic liquid-crystalline derivative of hexabenzocoronene [J].Adv. Mater., 1999, 11: 1469-1472.[8] Liu C Y, Fechtenktter A, Mark D W, et al. Room temperature discotic liquid crystalline thin films of hexa-peri-hexabenzocoronene: synthesis and optoelectronic properties [J].Chem. Mater., 2003, 15: 124-130.[9] Ana V, Donocadh P L, Paul J L, et al. Characterization and conductivity of langmuirblodgett films prepared from an amine-substituted oligo(phenylene ethynylene) [J]. Chem. Mater., 2008, 20: 258-264.[10] Hyatt J A. Organic preparations and procedures international: the new journal for organic synthesis [J]. Org. Prep. Proced. Int. , 1991, 23: 460-463.[11] Kbel C, Eckhardt K, Enkelmann V, et al. Synthesis and crystal packing of large polycyclic aromatic hydrocarbons: hexabenzo coronene and dibenzo phenanthro pentaphene [J]. J. Mater. Chem. , 2000, 10: 879-886.[12] Stabel A, Herwig P. Diodelike current-voltage curves for a single molecule-tunneling spectroscopy with submolecular resolution of an alkylated, peri-condensed hexabenzocoronene [J].Angew. Chem. Int. Ed. Engl., 1995, 34: 1609-1611.[13] Herwig P, Kayser W. Columnar mesophases of alkylated hexa-peri-hexabenzocoronenes with remarkably large phase widths [J]. Adv. Mater., 1996, 8: 510-513.[14] Kastler M, Pisula W, Wasserfallen D, et al. Influence of alkyl substituents on the solution- and surface-organization of hexa-peri-hexabenzocoronenes [J].J. Am. Chem. Soc., 2005, 127: 4286-4296.[15] Pisula W, Kastler M, Wasserfallen D, et al. Exceptionally long-range self-assembly of hexa-peri-hexabenzocoronene with dove-tailed alkyl substituents [J].J. Am. Chem. Soc., 2004, 126: 8074-8075.[16] Fechtenktter A, Saalwchter K, Harbison M A, et al. Highly ordered columnar structures from hexa-peri-hexabenzocoronenes-synthesis, X-ray diffraction, and solid-state heteronuclear multiple-quantum nmr investigations [J].Angew. Chem. Int. Ed., 1999, 38, 3039-3042.[17] Jishan W, Wojciech P, Klaus M.Graphenes as potential material for electronics [J]. Chem. Rev., 2007, 107(3): 718-747.[18] Piris J, Debije M G, Stutzmann N, et al. Aligned thin films of discotic hexabenzocoronenes: anisotropy in the optical and charge transport properties [J]. Adv. Funct. Mater., 2004, 74: 1053-1061.

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Luminescent discotic liquid crystals： from molecular design to applications

Synthesis of liquid crystals of non-chiral β-methylbutyl polybiphenyl isothiocyanate and high-frequency dielectric properties

Analysis for the dielectric properties of trans-cyclohexyl（tri）biphenyl liquid crystal compounds in microwave frequency bands

Synthesis and high frequency dielectric properties of low melting point triphenyl dialkyne liquid crystals

Synthesis and microwave properties of fluorinated terphenyl isothiocyanate liquid crystals

Related Author

YANG Xinyu

WANG Meng

YANG Hong

TU Youlan

ZHANG Lei

LEI Menglong

WU Shengli

LIU Haohao

Related Institution

College of Chemistry and Chemical Engineering， Southeast University

School of Electronic Science and Engineering， University of Electronic Science and Technology

Department of Chemistry and Environmental Engineering， Wuhan Polytechnic University

Guangzhou Haige Communication Group Incorporated Company

School of Electronic Science and Engineering, University of Electronic Science and Technology

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China 130033 Postal code：130033
Tel：0431-86176059 Email：yjxs@ciomp.ac.cn
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰