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Developing efficient heavy-atom-free photosensitizers applicable to TTA upconversion in polymer films.

ABSTRACT: Heavy-atom-free triplet photosensitizers are developed by harnessing the thermally active triplet state of carbazolyl dicyanobenzene (CDCB) derivatives and applied to realize visible-to-ultraviolet photon upconversion (UC) via triplet-triplet annihilation (TTA). Demonstrating an annihilator-appending strategy, the designed sensitizers effectively realize TTA UC in polyurethane films with 2,7-di-tert-butylpyrene (DBP) as the annihilator/emitter. The covalently tethered DBP to CDCB is proven critical for achieving the superior sensitizing and UC performance in the solid matrix, essentially by suppressing the reverse ISC and more effectively transferring triplet excitons to free emitters.

SUBMITTER: Peng J

PROVIDER: S-EPMC5975838 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Developing efficient heavy-atom-free photosensitizers applicable to TTA upconversion in polymer films.

Peng Jiang J Guo Xinyan X Jiang Xinpeng X Zhao Dahui D Ma Yuguo Y

Chemical science 20151109 2

Heavy-atom-free triplet photosensitizers are developed by harnessing the thermally active triplet state of carbazolyl dicyanobenzene (CDCB) derivatives and applied to realize visible-to-ultraviolet photon upconversion (UC) <i>via</i> triplet-triplet annihilation (TTA). Demonstrating an annihilator-appending strategy, the designed sensitizers effectively realize TTA UC in polyurethane films with 2,7-di-<i>tert</i>-butylpyrene (DBP) as the annihilator/emitter. The covalently tethered DBP to CDCB i ...[more]

PMID: 29910879

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Project description:Heavy-atom-free sensitizers forming long-living triplet excited states via the spin-orbit charge transfer intersystem crossing (SOCT-ISC) process have recently attracted attention due to their potential to replace costly transition metal complexes in photonic applications. The efficiency of SOCT-ISC in BODIPY donor-acceptor dyads, so far the most thoroughly investigated class of such sensitizers, can be finely tuned by structural modification. However, predicting the triplet state yields and reactive oxygen species (ROS) generation quantum yields for such compounds in a particular solvent is still very challenging due to a lack of established quantitative structure-property relationship (QSPR) models. In this work, the available data on singlet oxygen generation quantum yields (ΦΔ ) for a dataset containing >70 heavy-atom-free BODIPY in three different solvents (toluene, acetonitrile, and tetrahydrofuran) were analyzed. In order to build reliable QSPR model, a series of new BODIPYs were synthesized that bear different electron donating aryl groups in the meso position, their optical and structural properties were studied along with the solvent dependence of singlet oxygen generation, which confirmed the formation of triplet states via the SOCT-ISC mechanism. For the combined dataset of BODIPY structures, a total of more than 5000 quantum-chemical descriptors was calculated including quantum-chemical descriptors using density functional theory (DFT), namely M06-2X functional. QSPR models predicting ΦΔ values were developed using multiple linear regression (MLR), which perform significantly better than other machine learning methods and show sufficient statistical parameters (R=0.88-0.91 and q2 =0.62-0.69) for all three solvents. A small root mean squared error of 8.2 % was obtained for ΦΔ values predicted using MLR model in toluene. As a result, we proved that QSPR and machine learning techniques can be useful for predicting ΦΔ values in different media and virtual screening of new heavy-atom-free BODIPYs with improved photosensitizing ability.

Dataset Information

Developing efficient heavy-atom-free photosensitizers applicable to TTA upconversion in polymer films.

Publications

Developing efficient heavy-atom-free photosensitizers applicable to TTA upconversion in polymer films.

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