Fusing three perylenebisimide branches and a truxene core into a star-shaped chromophore with strong two-photon excited fluorescence and high photostability

Yuanpeng Xie, Xinfu Zhang, Yi Xiao, Youdi Zhang, Fan Zhou, Jing Qi, Junle Qu
2012 Chemical Communications  
S2 Materials and methods Compound 1 S1 , 2 S2 , PBI1 S3 , 6 S3 were synthesized according to literature methods. Compound 3 was synthesized on the basis of Scheme S1 according to literature methods. S4 All other reactants were purchased from commercial sources. NMR spectra were measured with a 400MHz Bruker spectrometer using TMS as reference for 1 H and 13 C NMR. Accurate mass correction is measured with MALDI Tof Mass Spectrometer (MALDI micro MX). Cyclic voltammetry (CV) was performed in
more » ... M solution in CH 2 Cl 2 with a standard commercial electrochemical analyzer in a three electrode single-component cell under argon with a scan rate of 100 mV/s. Working electrode: glassy carbon; reference electrode: Ag/AgCl; auxiliary electrode: Pt disk; internal standard: ferrocene (Fc). The energy of Fc/Fc + is 5.08 eV relative to vacuum. S5 UV-vis absorption spectrum is measured with UV-Vis Spectrophotometer (HP 8453). Fluorescence spectrum is measured with Fluorescence Lifetime Spectrometer (PTI-700). The fluorescence quantum yields were determined with Rhodamine 6G in ethanol as the reference. S6 Compound 4 and Tr-PBI were synthesized by employing sunlight as the catalyst and our group has reported the similar conversion. S7 The apparatus are very common and not tailor-made. Generally, the mixture of all reactant is added into a conical flask and a economical allihn condenser is connected to the flask. Then the flask is heated in a oil bath, and the whole apparatus is exposed to sunlight in sunny days. The needed sunlight is natural daylight without being filtered. Scheme S1 Synthetic routes of Compound 3 1) PPA(polyphosphoric acid), 60 , 0.5h; 2) acetic acid, concentrated hydrochloric acid, 100℃, 16h; 3) n-BuLi, n-C 6 H 13 Br, -78℃; 4) Br 2 , K 2 CO 3 , rt, 3h; 5) Pd(dppf)Cl 2 , bis(pinacolato)diboron, CH 3 COOK, toluene, 100℃,24h Electronic Supplementary Material (ESI) for Chemical Communications This journal is
doi:10.1039/c2cc31261a pmid:22447280 fatcat:rof4zrq4lje2hhr3yayfkwfgye