C-H Bond transformations for n-type semiconductors of functional fullerenes and fullerene segments

2015 Fiscal Year Final Research Report

• Project/Area Number: 25288043
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Tohoku University
• Principal Investigator: JIN Tienan 東北大学, 原子分子材料科学高等研究機構, 准教授 (80431493)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: C-H結合変換反応 / n型半導体 / 官能基化フラーレン / フラーレン部分骨格

Outline of Final Research Achievements

Bulk heterojunction solar cells, based on P3HT donor and the deuterated C60　acceptor, exhibited a higher photovoltaic performance as compared to the corresponding protonated C60 device. By using a new Mn-promoted C60-cycloadditon, the standard OPV acceptors, such as PCBM and ICBA, have been obtained in extraordinarily high yields. The Cu-catalyzed C-H amination of the monofunctionalized hydrofullerenes and Ni-catalyzed dibenzylation of C60 efficiently produced the monoamino- and dibenzyl-substituted 1,4-adducts, respectively. A novel Pd-catalyzed cascade crossover-annulation of o-alkynylarylhalides and diarylacetylenes has been developed for the synthesis of dibenzo[a,e]pentalenes. A novel Pd-catalyzed dual C－H activation of bis-biaryl alkynes produced important and useful products 9,9'BF derivatives in high yields. A novel FeCl3-mediated oxidative spirocyclization has been developed for construction of a new class of dispirolinked π-conjugated molecules.

Free Research Field

有機合成化学