Synthesis and characterization of 3,5-bis(2-hydroxyphenyl)-1,2,4-triazole functionalized tetraaryloxy perylene bisimide and metal-directed self-assembly

Yongjun Li; Ning Wang; Haiyang Gan; Huibiao Liu; Hao Li; Yuliang Li; Xiaorong He; Changshui Huang; Shuang Cui; Shu Wang; Daoben Zhu

doi:10.1021/jo051022c

Synthesis and characterization of 3,5-bis(2-hydroxyphenyl)-1,2,4-triazole functionalized tetraaryloxy perylene bisimide and metal-directed self-assembly

J Org Chem. 2005 Nov 25;70(24):9686-92. doi: 10.1021/jo051022c.

Authors

Yongjun Li¹, Ning Wang, Haiyang Gan, Huibiao Liu, Hao Li, Yuliang Li, Xiaorong He, Changshui Huang, Shuang Cui, Shu Wang, Daoben Zhu

Affiliation

¹ CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, PR China.

PMID: 16292795
DOI: 10.1021/jo051022c

Abstract

[structure: see text] New perylene bisimide dyes bearing 3,5-bis(2-hydroxyphenyl)-1,2,4-triazole receptor units with different spacers have been synthesized and characterized. The fluorescence and electronic properties of these compounds have been studied. MALDI-TOF, UV-vis, and fluorescence titration experiments proved that monotopic perylene bisimide ligands could be assembled into dimmers by Fe(III) coordination. The coordination properties of the ditopic perylene bisimide ligands have also been studied preliminarily. Furthermore, the SEM images indicated that well-defined nanoscale structures could be fabricated by self-assembly due to metal ion coordination and pi-pi stacking interactions of perylene rings with the help of a proper spacer.