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Preparation of Iodo-Bodipy dimer as triplet photosensitizers and Application in Photooxidation and Triplet-Triplet Annihilation (TTA) Upconversion
CUI Xiaoneng #,ZHAO Jianzhang *
State Key Laboratory of Fine Chemicals, Faculty of Chemical, Environmental and Biological Science and Technology, Dalian University of Technology, Dalian 116024, PR China
*Correspondence author
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Funding: The NSFC （No.21073028, 21273028, 21473020 and 21421005）, Dalian University of Technology for financial support （No.DUT2013TB07)）, Ministry of Education （No.SRFDP-20120041130005）, The Royal Society （No.UK) and NSFC）, The Fundamental Research Funds for the Central Universities （No.DUT14ZD226）
Opened online:11 August 2015
Accepted by: none
Citation: CUI Xiaoneng,ZHAO Jianzhang.Preparation of Iodo-Bodipy dimer as triplet photosensitizers and Application in Photooxidation and Triplet-Triplet Annihilation (TTA) Upconversion[OL]. [11 August 2015] http://en.paper.edu.cn/en_releasepaper/content/4651799
 
 
Iodo-boron dipyrromethene (Bis-bodipy) dimer (B-4I) was prepared as organic triplet photosensitizer for triplet-triplet annihilation (TTA) upconversion and photooxidation. We introduces four iodine atoms to the Bodipy chromophore, therefore the intersyster crossing (ISC) was improved compared to the single iodo-boron dipyrromethene. The organic photosensitizers show strong UV-vis absorptions at 490-590 nm. Long-lived triplet excited state (triplet lifetime up to 72.2 μs) is populated upon excitation of the photosensitizers, proved by nanosecond time-resolved transient absorption spectroscopy. The triplet state was located in the Bodipy part for B-4I by DFT caculations of spin density surface analysis. The singlet oxygen quantum yield is up to 90%, which is higher than traditional photosensitizers, such as tetraphenylporphyrin (TPP), Rose Bangel (RB) and Methylene Blue (MB). In the photooxidation reactions of 1,5-dihydroxy naphthalene, the product Juglone was obtained with high yield. The TTA upconversion was also studied with B-4I as the triplet photosensitizer and with perylene as triplet acceptor, the upconversion quantum yield is up to 5.76%.
Keywords:Photochemistry; DFT; Bodipy; Photooxidation; Triplet State; Upconversion
 
 
 

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