Goal

Development to obtain a propargyl compound with a base of triphenilamine and by a click reaction with thimyne derivates lead us to a macrocycle that can be used as a carryer capsule.

The tipe of base for the reaction dramatically influenced the yeld of cyclic oligomers, and potassium tert-butoxide was the most effective for the cyclization.The composition of the ciclic oligomers was determined by high-performance liquid chromatography (HPLC) as a mixture of pentamer, hexamer and heptamer. The cyclic pentamer was easily isolated by only recrystalization for tert-butyl methyl ether.

Synthesis

Figure 1

Aplications
Arylamine derivates have been widely applied to organic light-emitting diodes, photoconductors and photovoltaic devices because of their excellent electrical properties.

Cyclic oligomers composed of triphenylamine backbone were conveniently prepared via palladiumcatalized one-pot synthesis. The target compound were obtained by a click reaction with compound 3 and a triazide in presence of CuSO4 and TBTA.

Figure 2

Scheme 1

Scheme 2

Amine 1 was treated with NaBH4 to yeld tris(4hydroxy-methyl-phenyl)amine. Tris(4-formylphenyl)amine was synthesized from triphenylamine and POCl3. The cyclic pentamer was easily isolated by only recrystalization for tert-butyl methyl ether.

Conclusions
The target compound were obtained and the confirmation was make with a H-NMR spectra. High hole mobility and high photoconductivity of TPA backbone oers the possibility of being applied to organic photovoltaic devices. Because of electron-donating ability of the triphenylamine moiety, charge-transfer (CT) interaction with an electron acceptor can be a driving force for the cyclic oligomers to form inclusion complex. The condition for the preparation was optimized to give the cyclic oligomers with large ring sizes in good yeld up to 73%.

H-NMR Spectra of target compound

Guan Wang, Xinhai Zhang, Junlong Geng, Kai Li, Dan Ding, Kan-Yi Pu,Liping Cai, Yee-Hing Lai,and Bin Liu, Glycosylated Star-Shaped Conjugated Oligomers for Targeted Two-Photon Fluorescence Imaging, Chem. Eur. J., 2012,, 9705 9713 Kousuke Tsuchiya , Hiroko Miyaishi, Kenji Ogino, Facile preparation of macrocycles witht tryphenilamine backbone via C-N coupling reaction, Chem. Lett., 2011, 931-933