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Ladder‐Type Perylene Diimides Linked by Pyrene Bridges at Bay Area
Author(s) -
Ren Tianfei,
Shen Xiaoxiao,
Han Lingui,
Bai Libin,
Zhao Hongchi,
Wu Yonggang,
Wang Haijun,
Ba Xinwu
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201500034
Subject(s) - perylene , pyrene , bay , chemistry , environmental chemistry , environmental science , organic chemistry , engineering , molecule , civil engineering
A series of ladder‐type pyrene‐fused perylene diimides were designed and synthesized. To prepare the appropriate precursors, bromo‐perylene diimides and Bpin‐pyrene materials need to be coupled via Suzuki reaction. Whereas the Pd(PPh 3 ) 4 ‐catalyzed Suzuki reaction by heating was in low efficiency for the preparation of some precursors. For better yield, a microwave‐assisted Suzuki coupling reaction was used to prepare precursors. As expected, most of precursors were synthesized successfuly, however, the longest precursor was very difficult to obtain via Pd(PPh 3 ) 4 ‐catalyzed Suzuki reaction even under microwave‐assisted. When 1,1′‐bis(diphenylphosphino)ferrocene palladium dichloride (Pd(dppf)Cl 2 ) was empolyed as catalyst for Suzuki reaction, the longest precursor could be obtained in better yield. Subsequently the oxidative cyclization could smoothly proceed to form ladder structure with common catalyst 2,3‐dichloro‐5,5‐dicyano‐1,4‐benzoquinone /BF 3 •Et 2 O or FeCl 3 , and all ladder‐type perylene diimides exhibited high fluorescence quantum yield and bright red emission in solution, therefore could be good candidates for red emitting materials.