7-bromo-9,9-diethylfluorene-2-carbonitrile | 1239885-61-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7-bromo-9,9-diethylfluorene-2-carbonitrile
• 英文别名: 7-Bromo-9,9-diethylfluorene-2-carbonitrile
• CAS: 1239885-61-0
• 化学式: C₁₈H₁₆BrN
• 分子量: 326.236
• InChiKey: QQIONUDXMNUDTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-9,9-diethylfluorene-2-carbonitrile 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以81%的产率得到2,4,6-tris(7-bromo-9,9-diethylfluoren-2-yl)-1,3,5-triazine
  参考文献：
  名称：

  具有 1,3,5-三嗪核和取代芴臂的星形 D-A 化合物的电化学行为和电致化学发光

  摘要：

  我们报告了一系列星形供体-受体 (DA) 分子的合成、电化学和电致化学发光。星形分子由缺电子的 1,3,5-三嗪核组成，其中三个芴臂被二芳基氨基 (TAM1-TAM3) 或咔唑基 (TAM4) 电子供体取代。TAM1-TAM3 的循环伏安法表明，还原由一波单电子转移到核心组成，而氧化则表现出三个连续电子转移过程的单峰，并形成三阳离子。氧化后的含咔唑分子 TAM4 经历随后的快速化学反应以产生二聚体（通过两个自由基阳离子的整体偶联，同时失去两个质子）。二聚体比 TAM4 单体更容易电氧化。随着氧化侧的连续循环，在工作电极表面形成导电聚合物膜。由于受体（三嗪）中心和臂中强供体（二芳胺或咔唑）的存在，TAM1-TAM3 表现出很大的溶剂化变色效应，发射范围从深蓝色（428 nm）到橙红色（575 nm），具体取决于溶剂极性。这些星形分子显示出 0.70-0.81 的高 PL 量子产率。TAM1-TAM3

  DOI：

  10.1021/ja104160f
• 作为产物：
  描述：

  2,7-二溴-9,9-二乙基芴 在 ammonium hydroxide 、 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.25h， 生成 7-bromo-9,9-diethylfluorene-2-carbonitrile
  参考文献：
  名称：

  Two-photon absorbing polyhydroxy diphenylamino-dialkylfluorene-1,3,5-triazine molecules

  摘要：

  提供了以下结构式的新型2PA活性单体： 其中Y═H，丙烯酸或甲基丙烯酸基团；R是线性或支链烷基基团，—CmH2m+1，其中m=1-6或烷基醚基团，—(CH2CH2O)pMe，其中p=1-5。连接到三芳基胺基团的苯环上的R′—(OH)x基团的数量，可以是每个分子3个或6个，或含有3、4、5、6个的分子混合物，比例不同，其中x=1、2或3。R′是线性或支链烷基基团，如—CmH2m，其中m=1-6，即线性—(CH2)m，其中m=2-6，或支链烷基基团，如—CH2CH(R″)—，其中R″═—(CH2)lCH3，其中l=2-6。

  公开号：

  US08580958B1

文献信息

• Two-photon absorbing cross-linked polyurethanes containing delphenylamino-dialkyffluorene-1,3,5-triazine units
  申请人：The United States of America as represented by the Secretary of the Air Force

  公开号：US08318888B1

  公开（公告）日：2012-11-27

  Two-photon absorbing (2PA), cross-linked polyurethanes were prepared from bis(isocyanato) monomers, tris(isocyanato) monomers or a mixture of bis(isocyanato) and tris(isocyanato) monomers, in conjunction with a novel polyol molecules with donor-acceptor octupolar geometry, whose generic structure is comprised of an electron-accepting 1,3,5-triazine hub with three spokes constituted by electron-donating triarylalkylamine end-groups, which are polyfunctionalized with thermally reactive alcohol functions. The resulting neat glassy or rubbery solids are applicable in a wide range of linear & nonlinear optical applications.

  使用双光子吸收（2PA）交联聚氨酯，采用双异氰酸酯单体、三异氰酸酯单体或双异氰酸酯和三异氰酸酯单体混合物，结合具有给受体八极分子几何结构的新型聚醚分子制备而成。其通用结构由电子受体1,3,5-三嗪中心和由电子给体三芳基烷基胺末端组成的三个轴构成，这些轴通过热反应醇基多官能化。得到的整洁玻璃状或橡胶状固体适用于广泛的线性和非线性光学应用。
• SYNTHESIS OF TWO-PHOTON ABSORBING POLYHYDROXY DIPHENYLAMINO-DIALKYLFLUORENE-1,3,5-TRIAZINE MOLECULES
  申请人：Government of the United States as Represented by the Secretary of the Air Force

  公开号：US20140039185A1

  公开（公告）日：2014-02-06

  A method of synthesizing a two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound having the structure: where Y is hydrogen, a thermally self-polymerizable acrylic, or a methacrylic group; R is an alkyl group of the formula —C m H 2m+1 , wherein the subscript m ranges from 1 to 6, or an alkylether group of the formula —(CH 2 CH 2 O) p Me, wherein the subscript p ranges from 1 to 5; R′ is an alkyl group; and the R′—(OY) x groups are attached to the phenyl rings of the triarylamine moiety either in a para position or a meta position and the subscript x ranges from 1 to 3. The compound may be synthesized by (a) synthesizing a diarylamine intermediate, (b) synthesizing a brominated 1,3,5-triazine intermediate as a three-arm core structure, and (c) forming the two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound by covalently joining the diarylamine and each arm of the three-arm core structure and removing the acetone protecting groups. The diarylamine intermediate may be synthesized by protecting tris-1,1,1-(hydroxymethyl)ethane, via a ketal formation with acetone, as an acetonide derivative; furnishing bromophenoxy-methyltrimethyl-1,3-dioxane from the acetonide derivative; and arylating aniline with the bromophenoxy-methyltrimethyl-1,3-dioxane.

  一种合成具有结构的双光子活性三(diarylamino-9,9-二(R)芴基)-1,3,5-三嗪化合物的方法：其中Y为氢、热自聚丙烯酸或甲基丙烯酸基团；R为公式—CmH2m+1的烷基，其中下标m范围为1至6，或公式—(CH2CH2O)pMe的烷基醚基团，其中下标p范围为1至5；R'为烷基；而R'-（OY）x基团附着于三芳基胺基团的苯环的邻位或间位，其中下标x范围为1至3。该化合物可通过以下步骤合成：(a)合成二芳基胺中间体，(b)合成溴代1,3,5-三嗪中间体作为三臂核结构，(c)通过共价连接二芳基胺和三臂核结构的每个臂，去除丙酮保护基，形成双光子活性三(diarylamino-9,9-二(R)芴基)-1,3,5-三嗪化合物。二芳基胺中间体可以通过以下步骤合成：使用丙酮进行醇缩形成丙酮烯醇衍生物保护三-1,1,1-(羟甲基)乙烷为乙二醇缩合物；从乙二醇缩合物中得到溴苯氧甲基三甲基-1,3-二噁烷；然后用溴苯氧甲基三甲基-1,3-二噁烷进行芳基化反应。
• Synthesis of two-photon absorbing polyhydroxy diphenylamino-dialkylfluorene-1,3,5-triazine molecules
  申请人：The United States of America as Represented by the Secretary of the Air Force

  公开号：US08895730B2

  公开（公告）日：2014-11-25

  A method of synthesizing a two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound having the structure: where Y is hydrogen, a thermally self-polymerizable acrylic, or a methacrylic group; R is an alkyl group of the formula —CmH2m+1, wherein the subscript m ranges from 1 to 6, or an alkylether group of the formula —(CH2CH2O)pMe, wherein the subscript p ranges from 1 to 5; R′ is an alkyl group; and the R′—(OY)x groups are attached to the phenyl rings of the triarylamine moiety either in a para position or a meta position and the subscript x ranges from 1 to 3. The compound may be synthesized by (a) synthesizing a diarylamine intermediate, (b) synthesizing a brominated 1,3,5-triazine intermediate as a three-arm core structure, and (c) forming the two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound by covalently joining the diarylamine and each arm of the three-arm core structure and removing the acetone protecting groups. The diarylamine intermediate may be synthesized by protecting tris-1,1,1-(hydroxymethyl)ethane, via a ketal formation with acetone, as an acetonide derivative; furnishing bromophenoxy-methyltrimethyl-1,3-dioxane from the acetonide derivative; and arylating aniline with the bromophenoxy-methyltrimethyl-1,3-dioxane.

  一种合成双光子活性三(diarylamino-9,9-di(R)fluorenyl)-1,3,5-三嗪化合物的方法，其结构为：其中Y为氢，热自聚合丙烯酸或甲基丙烯酸基团;R为公式—CmH2m+1的烷基，其中下标m范围从1到6，或公式—(CH2CH2O)pMe的烷醚基团，其中下标p范围从1到5;R′为烷基;且R′—(OY)x基团连接到三芳胺基团的苯环中的对位或间位，其中下标x范围从1到3。该化合物可以通过(a)合成二芳胺中间体，(b)合成溴代1,3,5-三嗪中间体作为三臂核心结构，以及(c)通过共价连接二芳胺和三臂核心结构的每个臂并去除丙酮保护基形成双光子活性三(diarylamino-9,9-di(R)fluorenyl)-1,3,5-三嗪化合物。二芳胺中间体可以通过将三-1,1,1-(羟甲基)乙烷保护为丙酮缩醛衍生物，提供溴苯氧甲基三甲基-1,3-二噁烷衍生物，以及用溴苯氧甲基三甲基-1,3-二噁烷芳基化苯胺来合成。
• Two-photon absorbing cross-linked polyurethanes containing diphenylamino-dialkylfluorene-1,3,5-triazine units
  申请人：The United States of America, as represented by the Secretary of the Air Force

  公开号：US08735528B1

  公开（公告）日：2014-05-27

  Two-photon absorbing (2PA), cross-linked polyurethanes were prepared from bis(isocyanato) monomers, tris(isocyanato) monomers or a mixture thereof, in conjunction with novel polyol molecules with donor-acceptor octupolar geometry, whose generic structure is comprised of an electron-accepting 1,3,5-triazine hub with three spokes constituted by electron-donating triarylalkylamine end-groups, which are polyfunctionalized with thermally reactive alcohol functions. The resulting neat glassy or rubbery solids are applicable in a wide range of linear and nonlinear optical applications.

  使用双光子吸收（2PA）交联聚氨酯制备自双（异氰酸酯）单体，三（异氰酸酯）单体或其混合物，与具有给受体八极几何的新型聚醚分子相结合，其通用结构包括由电子捐赠三芳基烷基胺末端基团构成的三个辐条，这些基团通过热反应醇基多官能化。所得到的整齐无缝的玻璃状或橡胶状固体适用于广泛的线性和非线性光学应用。
• POLYCYCLIC COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING SAME
  申请人：LG Chem, Ltd.

  公开号：EP2876104B1

  公开（公告）日：2018-09-05