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

Isao Yamaguchi, Kenta Tsuchie

Department of Chemistry, Interdisciplinary Graduate School of Faculty of Science and Engineering, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan.

DOI: 10.4236/ijoc.2012.23027                

Abstract

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.

Keywords

Hexaphenylbenzene; Indeno[1, 2-b]fluorene; Donor Number; Photoluminescence; Solvatochromism

Conflicts of Interest

The authors declare no conflicts of interest.

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