Supporting Information For s4

Supplementary material for

The Impact of Trans/Cis Photoisomerization on Photoinduced Electron Transport between 4, 4’-Stilbenedicarboxlic Acid and Columnar Perylenediimide Aggregates in Water

Ruimin Zhu, Yingyuan Zhao, Tingting Sun, Heyuan Liu, Ying Zhang, and Xiyou Li*

Key lab for colloid and interface chemistry, Ministry of Education, Department of chemistry, Shandong University, Jinan 250100, China

1.  Synthesis of PDI-I

1.1  Synthesis of bis (2-(dimethylamino) ethyl)perylene diimide

The 3,4,9,10-perylenetetracarboxylic acid dianhydride (1.082g, 2.757 mmol), 2-(dimethylamino)ethyl amine (0.987g, 11.20 mmol) and imidazole (14.113g, 207 mmol) were added to round bottom flask and heated to 130℃ under a nitrogen atmosphere and kept at the temperature for 3h. Then methanol was dropped into the flask before it was cooled to room temperature. Precipitates were found and the solid was collected by filtration and then washed by methanol for three times and dried in vaccum at 60℃ for 4h. The product was obtained as dark purple solid (1.455g, 99%).

1H NMR (400 MHz, CDCl3): d2.38 (s, 12H), d 2.70 (t, 4H), d 4.37 (t, 4H), d 8.64(d, 4H), d 8.69 (d, 4H).

1.2  Synthesis of bis (2-(trimethylammonium) ethyl)perylene diimide

Bis(2-(dimethylamino)ethyl)perylene diimide (0.302g, 0.566mmol) was dissolved in 20 mL toluene and the solution of CH3I (0.25 mL, 4.08mmol) in 5 mL toluene was added. The mixture was refluxed for 3h under a nitrogen atmosphere and then filtered. The solid was washed by chlorform until the filtrate was colorless. The pure product (0.443g, 96%) was obtained after reflux in chlorform for another several hours and drying at vaccum at 60℃ for 4h. 1H NMR (400 MHz, DMSO-d6): d 3.25(s, 18H), d 3.67(t, 4H), d 4.51(t, 4H), d 8.62(d,4H), d 8.99(d, 4H).


Figure S1. Absorption spectra of trans-SDBA (10 mM ) under the radiation of Xe lamp with a 310 nm optical filter for different times.

Figure S2. Differential pulse voltammogram of SDBA in lye of KOH containing 0.1 M Na2SO4.

Figure S3. Absorption spectra of 10 mM PDI-I in water and methanol.