六（十二烷基）六苯并蒄的简便合成

陈键; 杜渭松; 高潮

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六（十二烷基）六苯并蒄的简便合成

材料物理和化学 | 更新时间：2020-08-12

- 六（十二烷基）六苯并蒄的简便合成
- Simply synthesis of hexakis(4-dodecy)-peri-hexabenzocoronene
- 液晶与显示 2014年29卷第4期页码：508-514
- 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：
  
  国家自然科学基金（No：60907012，No.61177031）()
- DOI：
  中图分类号：
- 收稿日期：2013-12-29，
  
  修回日期：2014-01-15，
  
  纸质出版日期：2014-08-05
- 稿件说明：
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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.

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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.

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