Synthesis and Solvatochromic Behavior of Hexaphenylbenzenes and Indeno[1,2-<i>b</i>]fluorene Derivatives with Hydroxy Groups  

作　　者：Isao Yamaguchi Kenta Tsuchie 

机构地区：[1]Department of Chemistry, Interdisciplinary Graduate School of Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan

出　　处：《International Journal of Organic Chemistry》2012年第3期178-187,共10页有机化学国际期刊（英文）

摘　　要：Hexakis(4-methoxyphenyl)benzene (HPB-OMe(1)) and hexakis(2,6-dimethyl-4-methoxyphenyl)benzene (HPB-OMe(2)) were synthesized via organometallic complex catalysis. The treatment of HPB-OMe(1) with FeCl3 caused cyclodehydrogenation at two positions to yield an oligophenylene with an indeno[1,2-b]fluorene structure (IF-OMe). Deprotection of the methoxy groups of these compounds was conducted by treatment with BBr3. Deprotonation of the OH groups of HPB-OH(1), HPB-OH(2), and IF-OH through treatment with NaH caused a bathochromic shift in the absorption and photoluminescence (PL) peaks. The bathochromic shift of the deprotonated species increased with the donor number (DN) of the solvents. These observations can be explained as the consequence of intramolecular charge transfer (ICT) from the ONa groups to the inner benzene rings.Hexakis(4-methoxyphenyl)benzene (HPB-OMe(1)) and hexakis(2,6-dimethyl-4-methoxyphenyl)benzene (HPB-OMe(2)) were synthesized via organometallic complex catalysis. The treatment of HPB-OMe(1) with FeCl3 caused cyclodehydrogenation at two positions to yield an oligophenylene with an indeno[1,2-b]fluorene structure (IF-OMe). Deprotection of the methoxy groups of these compounds was conducted by treatment with BBr3. Deprotonation of the OH groups of HPB-OH(1), HPB-OH(2), and IF-OH through treatment with NaH caused a bathochromic shift in the absorption and photoluminescence (PL) peaks. The bathochromic shift of the deprotonated species increased with the donor number (DN) of the solvents. These observations can be explained as the consequence of intramolecular charge transfer (ICT) from the ONa groups to the inner benzene rings.

关 键 词：Hexaphenylbenzene Indeno[1 2-b]fluorene DONOR Number Photoluminescence SOLVATOCHROMISM 

分 类 号：O6[理学—化学]