1,5-bis(4,6-dichloro-1,3,5-triazin-2-ylamino)-naphthalene | 1042995-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,5-bis(4,6-dichloro-1,3,5-triazin-2-ylamino)-naphthalene
• 英文别名: N¹,N⁵-bis(4,6-dichloro-1,3,5-triazin-2-yl)naphthalene-1,5-diamine；1-N,5-N-bis(4,6-dichloro-1,3,5-triazin-2-yl)naphthalene-1,5-diamine
• CAS: 1042995-76-5
• 化学式: C₁₆H₈Cl₄N₈
• 分子量: 454.105
• InChiKey: CCKFYRXQXLOJTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  吗啉 、 1,5-bis(4,6-dichloro-1,3,5-triazin-2-ylamino)-naphthalene 以 neat (no solvent) 为溶剂， 反应 0.17h， 以85%的产率得到N¹,N⁵-bis[4,6-dimorpholino-1,3,5-triazin-2-yl]naphthalene-1,5-diamine
  参考文献：
  名称：

  Green synthesis of luminescent blue emitters based on bistriazines with naphthalene as a π-conjugated spacer

  摘要：

  A new series of luminescent blue emissive bistriazines is described. Bistriazines with a naphthalene spacer were prepared using a green methodology that involved microwave irradiation, solvent free conditions and a reaction time of only 10 min. The synthesis was followed by a simple purification procedure. D-sigma-A-sigma-pi-sigma-A-sigma-D systems were constructed using 1,5-naphthylidene as a planar pi-bridge and different donor substituents were attached to the triazine ring. UV-vis and fluorescence spectroscopy showed that the increased conjugation in bistriazines with respect to monotriazines resulted in a 40-fold increase in the photoluminescence quantum yield (Phi(F)). The bistriazines were efficient blue emitters with Phi(F) values up to 0.87. The aggregation behavior and the optical and thermal properties of these systems have been studied. The bistriazines showed good thermal stability in conjunction with high Phi(F) values and they are therefore very promising materials for use in optoelectronic devices. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.09.009
• 作为产物：
  描述：

  三聚氯氰 、 1,5-萘二胺 在 NaCO₃ 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以90%的产率得到1,5-bis(4,6-dichloro-1,3,5-triazin-2-ylamino)-naphthalene
  参考文献：
  名称：

  Synthesis of 1,5-bis(4,6-dichloro-1,3,5-triazinylamino)naphthalene and its application to spectrofluorimetric determination of aniline

  摘要：

  A new fluorescent reagent 1,5-bis(4,6-dichloro-1,3,5-triazinylamino)naphthalene (DTAN) was synthesized. The optimum conditions of fluorescent reaction of this reagent with aniline (PA) were also investigated. Based on this reaction, a new spectrofluorimetric method was developed for the determination of aniline. The fluorescent intensity was directly proportional to the concentration of aniline in the ranges 0.05-2.0 mu g mL(-1) and 2.0-50 mu g mL(-1) with the detection limits of 34 ng mL(-1) and 90 ng mL(-1). This method is simple, practical and can afford good precision and accuracy and can be successfully applied to assess aniline in water samples. A possible mechanism of the change of fluorescence intensity introduced by putting the aniline into the system is also discussed. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2007.10.032

文献信息

• Green synthesis of luminescent blue emitters based on bistriazines with naphthalene as a π-conjugated spacer
  作者：José R. Ramírez、Amparo Ruiz-Carretero、María A. Herrero、Ana Sánchez-Migallón、Antonio de la Hoz

  DOI：10.1016/j.dyepig.2015.09.009

  日期：2016.1

  A new series of luminescent blue emissive bistriazines is described. Bistriazines with a naphthalene spacer were prepared using a green methodology that involved microwave irradiation, solvent free conditions and a reaction time of only 10 min. The synthesis was followed by a simple purification procedure. D-sigma-A-sigma-pi-sigma-A-sigma-D systems were constructed using 1,5-naphthylidene as a planar pi-bridge and different donor substituents were attached to the triazine ring. UV-vis and fluorescence spectroscopy showed that the increased conjugation in bistriazines with respect to monotriazines resulted in a 40-fold increase in the photoluminescence quantum yield (Phi(F)). The bistriazines were efficient blue emitters with Phi(F) values up to 0.87. The aggregation behavior and the optical and thermal properties of these systems have been studied. The bistriazines showed good thermal stability in conjunction with high Phi(F) values and they are therefore very promising materials for use in optoelectronic devices. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of 1,5-bis(4,6-dichloro-1,3,5-triazinylamino)naphthalene and its application to spectrofluorimetric determination of aniline
  作者：Wei Wei、Hong-Jian Wang、Chong-Qiu Jiang

  DOI：10.1016/j.saa.2007.10.032

  日期：2008.7

  A new fluorescent reagent 1,5-bis(4,6-dichloro-1,3,5-triazinylamino)naphthalene (DTAN) was synthesized. The optimum conditions of fluorescent reaction of this reagent with aniline (PA) were also investigated. Based on this reaction, a new spectrofluorimetric method was developed for the determination of aniline. The fluorescent intensity was directly proportional to the concentration of aniline in the ranges 0.05-2.0 mu g mL(-1) and 2.0-50 mu g mL(-1) with the detection limits of 34 ng mL(-1) and 90 ng mL(-1). This method is simple, practical and can afford good precision and accuracy and can be successfully applied to assess aniline in water samples. A possible mechanism of the change of fluorescence intensity introduced by putting the aniline into the system is also discussed. (C) 2007 Elsevier B.V. All rights reserved.