naphtho[2,3-b:6,7-b']difuran | 1193435-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: naphtho[2,3-b:6,7-b']difuran
• 英文别名: naphtho-[2,3-b;5,6-b']difuran；Naphtho[2,3-b:6,7-b']difuran；[1]benzofuro[6,5-f][1]benzofuran
• CAS: 1193435-27-6
• 化学式: C₁₄H₈O₂
• 分子量: 208.216
• InChiKey: PPFYLQZIACBIGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,6-diacetoxy-3,7-bis(trimethylsilylethynyl)naphthalene 在 水 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以45%的产率得到naphtho[2,3-b:6,7-b']difuran
  参考文献：
  名称：

  Naphtho[2,3-b:6,7-b′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices

  摘要：

  New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C-60 or C-70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm(2) V-1 s(-1) and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.

  DOI：

  10.1021/cm202853b

文献信息

• [EN] ELECTROACTIVE COMPOUNDS<br/>[FR] COMPOSÉS ÉLECTROACTIFS
  申请人：DU PONT

  公开号：WO2017210072A1

  公开（公告）日：2017-12-07

  There is provided a compound having Formula (I): (I). In the formula: NpHet is a naphthalene core having at least one fused 5-membered heteroaromatic ring, where the heteroaromatic ring has one heteroatom which is O, S, Se, or Te; Ar1-Ar6 are the same or different and are a hydrocarbon aryl group, a heteroaryl group, or a deuterated analog thereof; a and b are the same or different and are 0 or 1; m and n are the same or different and are 0 or 1; with the proviso that a, b, m, and n are not all 0.

  提供一种具有化学式(I)的化合物：(I)。在该式中：NpHet是至少具有一个融合的5元杂芳环的萘核，其中杂芳环具有一个杂原子，该杂原子是O、S、Se或Te；Ar1-Ar6相同或不同，是一个碳氢芳基团、一个杂芳基团或其氘代物；a和b相同或不同，为0或1；m和n相同或不同，为0或1；但要求a、b、m和n不全为0。
• [EN] COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL CONTAINING SAME, ORGANIC SEMICONDUCTOR INK, AND ORGANIC TRANSISTOR<br/>[FR] COMPOSÉ, MATÉRIAU SEMI-CONDUCTEUR ORGANIQUE LE CONTENANT, ENCRE SEMI-CONDUCTRICE ORGANIQUE ET TRANSISTOR ORGANIQUE<br/>[JA] 化合物、並びにそれを含有する有機半導体材料、有機半導体インク及び有機トランジスタ
  申请人：DAINIPPON INK & CHEMICALS

  公开号：WO2015137304A1

  公开（公告）日：2015-09-17

  本発明の課題は、溶剤への溶解性に優れ、複雑なプロセスを経由せずとも容易に、高い移動度の膜を与える、下記一般式（１）で表される化合物、及びそれを用いた有機半導体材料を提供すること、更には、実用的な構成の有機トランジスタを簡便に作製できる有機半導体インクを提供することである。特定の置換基を有するメソゲン骨格からなる化合物は、溶剤溶解性に優れる故に有機半導体インクとしての適性を有し、煩雑な熱処理を必要とせず、簡便な湿式法であっても、上記課題を解決する。上記一般式（１）中のＲ１，Ｒ２，ｐ，ＭＳＧは、請求項１に記載のとおりである。
• Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]dichalcogenophenes: Syntheses, Characterizations, and Chalcogene Atom Effects on Organic Field-Effect Transistor and Organic Photovoltaic Devices
  作者：Masahiro Nakano、Hiroki Mori、Shoji Shinamura、Kazuo Takimiya

  DOI：10.1021/cm202853b

  日期：2012.1.10

  New linear-shaped naphtho[2,3-b:6,7-b']-difurans (NDFs) and -selenophenes (NDSs) were synthesized selectively from 3,7-dibromo-2,6-dihydroxynaphthalene and evaluated as organic semiconductors in comparison to corresponding naphtho[2,3-b:6,7-b']dithiophenes (NDTs). Evaluation of the electronic structures of the parent compounds by means of electrochemical and optical measurements clearly indicated that NDT and NDS are quite similar to each other, whereas only NDF has a marked different electronic structure. Thin film devices, including organic field-effect transistors (OFETs) and bilayer photovoltaics (OPVs) with C-60 or C-70 as an acceptor layer, were fabricated with the diphenyl derivatives using vacuum deposition. The thin films were found to be nicely crystalline with the edge-on molecular orientation both on Si/SiO2 (for OFETs) and ITO substrates (for OPVs). The thin films acted as active semiconducting layer in OFETs with mobility higher than 0.1 cm(2) V-1 s(-1) and as a donor layer in OPVs with power conversion efficiencies of up to 2.0%, indicating that the present naphthodichalcogenophenes are potential core structures for the development of new organic semiconductors.