Regioregular head-to-tail oligothiophene-functionalized 9,9   &apos;-spirobifluorene derivatives. 2. NMR characterization, thermal   behaviors, and electrochemical properties

doi:10.1021/jo020397k

CORC > 北京大学 > 化学与分子工程学院

	Regioregular head-to-tail oligothiophene-functionalized 9,9 '-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties
	Pei, J ; Ni, J ; Zhou, XH ; Cao, XY ; Lai, YH
刊名	journal of organic chemistry
	2002
关键词	AMORPHOUS MOLECULAR MATERIALS ALKYL-SUBSTITUTED OLIGOTHIOPHENES LIGHT-EMITTING-DIODES ORGANIC-DYE GLASSES STARBURST MOLECULES THERMODYNAMIC PARAMETERS CONDUCTING POLYMERS THIOPHENE OLIGOMERS CONJUGATED POLYMERS STABILITY
DOI	10.1021/jo020397k
英文摘要	Oligothiophene-functionalized 9,9'-spirobifluorene derivatives exhibit good solubility in polar organic solvents, especially compounds 5a-d to 7a-d due to the introduction of the flexible, n-hexyl chain. The structures of all compounds studied are characterized and verified by H-1 and C-13 NMR spectra. The results not only show that these organic conjugated materials with no substituents or n-hexyl substituents are successfully synthesized through the corresponding synthetic methodologies, but also prove that chemical shifts of protons and carbons in the aromatic range change with the attachment and the increase of the thiophene ring at the 9,9'-spirobifluorene fragment. The thermal analysis results demonstrate that these compounds are quite stable, and evaporate from 300 to 700 degreesC. Most of these compounds exhibit a stable amorphous state in the solid state. The electrochemical properties of all compounds studied are also investigated. The results indicate that radical cation behaviors of oligothiophene-modified 9,9'-spirobifluorene derivatives are more stable than those of normal oligothiophenes, that oxidative and reductive peak potentials shift cathodically or anodically, and that the HOMO and LUMO energy levels are also tuned with the increase of the thiophene ring owing to the enhanced pi-electron delocalization and the increasing conjugation length. Oxidative potentials of nonsubstituted oligothiophene-functionalized 9,9'-spirobifluorene derivatives are more sensitive to the increase of thiophene rings than those of 9,9'-spirobifluorene derivatives with n-hexyl groups. The energy levels and band gaps of all compounds studied are also calculated from the onset potentials of n-doping and p-doping and are adjusted by varying thiophene oligomers and their attachment patterns to the 9,9'-spirobifluorene ring to make them suitable for the work functions of the electrodes.; Chemistry, Organic; SCI(E); EI; 50; 23; 8104-8113; 67
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/150379]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Pei, J,Ni, J,Zhou, XH,et al. Regioregular head-to-tail oligothiophene-functionalized 9,9 '-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties[J]. journal of organic chemistry,2002.
APA	Pei, J,Ni, J,Zhou, XH,Cao, XY,&Lai, YH.(2002).Regioregular head-to-tail oligothiophene-functionalized 9,9 '-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties.journal of organic chemistry.
MLA	Pei, J,et al."Regioregular head-to-tail oligothiophene-functionalized 9,9 '-spirobifluorene derivatives. 2. NMR characterization, thermal behaviors, and electrochemical properties".journal of organic chemistry (2002).