9-Anthryl-capped DPP-based dyes: aryl spacing induced differential optical properties

摘要: While pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-diones (DPPs) are extensively used as building blocks in field-effect transistors and photovoltaic active layers, less attention has been paid to the construction of novel optical materials. In this work, we have designed synthesized two soluble 9-anthryl-capped DPP derivatives with benzene thiophene spacing units, 1,4-diketo-2,5-dioctyl-3,6-bis(9-anthrylphenyl)pyrrolo[3,4-c]pyrrole (ABDPP) 1,4-diketo-2,5-dioctyl-3,6-bis(9-anthrylthiophen)pyrrolo[3,4-c]pyrrole (ATDPP). It is found that ABDPP ATDPP emit strong weak fluorescence solution, respectively, but their crystalline states all exhibit fluorescence, implying only exhibits an aggregation-enhanced emission (AEE) effect although dyes adopt a twisted conjugation backbone. Interestingly, grinding pressing can change color from yellow red, contributing non-AEE dye exhibiting mechanochromic luminescence. Differential scanning calorimetry powder X-ray diffraction analyses confirm phase transition between amorphous upon application external stimuli responsible for reversible change. This work demonstrated once again subtle manipulation molecular structure unit could significantly tune alter properties conjugated organic