Microwave-Assisted Selective Synthesis of Mono- and Bistriazines with 蟺-Conjugated Spacers and Study of the Optoelectronic Properties

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• 作者：A. Ruiz-Carretero ; O. Noguez ; T. Herrera ; J. R. Ram铆rez ; A. S谩nchez-Migall贸n ; A. de la Hoz
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：79
• 期：11
• 页码：4909-4919
• 全文大小：462K
• 年卷期：v.79,no.11(June 6, 2014)
• ISSN：1520-6904

文摘

A series of mono- and bistriazine derivatives were selectively prepared in high yields using microwave irradiation. Donor substituents were attached on the triazine ring, including pyrazolyl-substituted anilines and o-, m-, and p-phenylenediamine as 蟺-conjugated spacers. This method was used to build 蟽鈥撓€鈥撓冣€揂鈭捪冣€揇 systems for monotriazines and D鈭捪冣€揂鈭捪冣€撓€鈥撓冣€揂鈭捪冣€揇 systems for bistriazines. A study of the optoelectronic properties was performed by UV鈥搗is and fluorescence spectroscopy and cyclic voltammetry. The monotriazines do not show any emission, but the bistriazines are blue emitters and show an interesting solvatochromic effect with large Stokes shifts of more than 10鈥?00 cm<sup>鈥?sup> in some cases and quantum yields up to 23%. The optoelectronic properties depend on the conjugation and the position and donor character of the substituents and spacers. Cyclic voltammetry was used to determine the energy levels (HOMO and LUMO) in the bistriazines. An increase in the energy of the HOMO and a decrease in the energy of the LUMO were observed upon extending the conjugation. The title compounds showed interesting properties for use in optoelectronic devices, especially as blue emitters.