ICCAS OpenIR
Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures
Song, Yabin1,2; Di, Chong-an1,2; Wei, Zhongming1,2; Zhao, Tianyue1,2; Xu, Wei1; Liu, Yunqi1; Zhang, Deqing1; Zhu, Daoben1
2008
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
ISSN0947-6539
Volume14Issue:15Pages:4731-4740
AbstractTwo cyclic carbazolenevinylene dimers 1 and 2 were synthesized by McMurry coupling reactions. A linear compound 3 was also prepared for comparison. Compounds 1-3 were fully characterized by means of NMR spectroscopy, HRMS, elemental analysis, and UV/Vis absorption spectroscopy. Quantum chemical simulations showed that the cyclic compounds possessed smaller HOMO-LUMO gaps and more extended conjugation. The UV/Vis absorption spectra of the cyclic compounds showed blueshifts compared with that of the linear compound 3. Time-dependent DFT (TD-DFT) analysis revealed that this was due to the different selection rules for molecules with cyclic and linear architectures. The cyclic conformation also significantly affected the molecular ordering in the solid state. The X-ray crystal structure of 1. showed partial pi-pi overlapping between the adjacent molecules. Thin films of 1-3 were fabricated by the vacuum-deposition method on Si/SiO2 substrates. Multi crystalline thin films were obtained from compounds 1 and 2, but only amorphous thin films could be obtained for the linear compound 3. Another important difference between the cyclic and linear compounds was the reduced reorganization energy for the cyclic compounds. These two facts have resulted in improved field-effect transistor (FET) mobilities for the cyclic compounds compared with the linear compound. In addition, as the substrate temperature has a significant influence on the morphology and the degree of crystallinity of the thin films deposited, the device performance could be optimized by varying the substrate temperature. The FET devices based on 2 gave the highest mobility of 0.013 cm(2)V(-1)s(-1). The results showed that carbazole derivatives with cyclic structures might make better FETs.
KeywordCyclooligornerization Density Functional Calculations Films Semiconductors Structure-activity Relationship
DOI10.1002/chem.200800008
Indexed BySCI ; IC
Language英语
WOS IDWOS:000256241700032
PublisherWILEY-V C H VERLAG GMBH
Citation statistics
Cited Times:37[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/64912
Collection中国科学院化学研究所
Corresponding AuthorXu, Wei
Affiliation1.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Organ Solids, Beijing 100080, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Song, Yabin,Di, Chong-an,Wei, Zhongming,et al. Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures[J]. CHEMISTRY-A EUROPEAN JOURNAL,2008,14(15):4731-4740.
APA Song, Yabin.,Di, Chong-an.,Wei, Zhongming.,Zhao, Tianyue.,Xu, Wei.,...&Zhu, Daoben.(2008).Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures.CHEMISTRY-A EUROPEAN JOURNAL,14(15),4731-4740.
MLA Song, Yabin,et al."Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures".CHEMISTRY-A EUROPEAN JOURNAL 14.15(2008):4731-4740.
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