The impact of trans/cis photoisomerization on photoinduced electron transport between 4,4′-stilbenedicarboxylic acid and columnar perylenediimide aggregates in water

Abstract

Photoinduced electron transfer (PET) between s e l f -a s s e m b l e d t r a n s -or c i s -i s o m e r o f 4 , 4 ′ -s t i l b e n e d i c a r b o x y l i c a c i d ( S D B A ) a n d [ N , N ′ -di(2-(trimethylammoniumiodide)ethylene)]perylenediimide(PDI-I) in water has been investigated. Both trans-SDBA and cis-SDBA molecules can form stable complexes with columnar PDI-I aggregates in water with a 1:1 stoichiometry via ionic interactions, but the complex of cis-isomer is more stable as revealed by the UV-vis absorption and fluorescence spectroscopy. The electrochemical experiments suggest that cis-SDBA is a better electron donor than its trans-isomer. However, fluorescence quenching experiments suggest that the electron transfer from trans-SDBA is more efficient than that from cis-SDBA, which is obviously contradictory to the results of binding constant and the electrochemical experiments. The contradictory results can be attributed to that the columnar aggregates (PDI-I) n are utterly destroyed in cis-SDBA-(PDI-I) n system caused by stronger ionic interaction between cis-SDBA and (PDI-I) n . Also, the bending conformation of cis-SDBA probably results in a larger distance between cis-SDBA and the surface of (PDI-I) n . The results of this research suggest that the electron transfer can be tuned by the aggregation and/or configuration of the donors and acceptors.

Self-sorted photoconductive xerogels

“…We chose a stilbene-based gelator ( 2 , Fig. 2 ) as a potential donor as electron transfer from stilbenes to photoexcited PBIs has been shown to be possible previously 33 , 34 and in line with these reports we find a broad redox feature from +0.4 to +0.8 V Ag/AgCl that could potentially act as an electron donor to a photoexcited PBI. In solution at pH 9 significant aggregation of both 1 and 2 occurs which may give rise to the poorly defined electrochemical features.…”

“… 27 We expect that the photoresponse will be highly dependent on the structure and environment of the materials and on the available charge transfer pathways. Therefore, we explored if inclusion of 2 as a known charge acceptor/donor system 33 , 34 , 50 is able to modify the photoresponse of 1 by comparing xerogel- 1 , 2 with xerogel- 1 . To do this, thin films were prepared using a mask and measured in air.…”

Surface Decorating of CH3NH3PbBr3 Nanoparticles with the Chemically Adsorbed Perylenetetracarboxylic Diimide

“…Perylenetetracarboxylic diimides (PDIs), a special class of organic dyes with outstanding photochemical and photophysical property and photostability, are commonly applied in various optoelectronic devices as semiconductors or electron acceptors. − In addition, characteristic absorption of PDIs around 500–600 nm can make up for the low absorption of CH 3 NH 3 PbBr 3 at this range. Therefore, PDI molecules are ideal candidates to replace OA to be anchored on the surface of CH 3 NH 3 PbBr 3 NPs.…”