Perylene-Derived Triplet Acceptors with Optimized Excited State Energy Levels for Triplet鈥揟riplet Annihilation Assisted Upconversion

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• 作者：Xiaoneng Cui ; Azzam Charaf-Eddin ; Junsi Wang ; Boris Le Guennic ; Jianzhang Zhao ; Denis Jacquemin
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：March 7, 2014
• 年：2014
• 卷：79
• 期：5
• 页码：2038-2048
• 全文大小：697K
• 年卷期：v.79,no.5(March 7, 2014)
• ISSN：1520-6904

文摘

A series of perylene derivatives are prepared as triplet energy acceptors for triplet鈥搕riplet annihilation (TTA) assisted upconversion. The aim is to optimize the energy levels of the T₁ and S₁ states of the triplet acceptors, so that the prerequisite for TTA (2E_T1 > E_S1) can be better satisfied, and eventually to increase the upconversion efficiency. Tuning of the energy levels of the excited states of the triplet acceptors is realized either by attaching aryl groups to perylene (via single or triple carbon鈥揷arbon bonds), or by assembling a perylene-BODIPY dyad, in which the components present complementary S₁ and T₁ state energy levels. The S₁ state energy levels of the perylene derivatives are generally decreased compared to perylene. The anti-Stokes shift, TTA, and upconversion efficiencies of the new triplet acceptors are improved with respect to the perylene hallmark. For the perylene-BODIPY dyads, the fluorescence emission was substantially quenched in polar solvents. Moreover, we found that extension of the 蟺-conjugation of BODIPY energy donor significantly reduces the energy level of the S₁ state. Low S₁ state energy level and high T₁ state energy level are beneficial for triplet photosensitizers.