MACROMOLECULAR DIKETOPYRROLOPYRROLE AS THE ANNIHILATOR IN UPCONVERTING ORGANIC FILMS

Barbara Chatinovska1, Augustina Jozeliūnaitė1, Edvinas Radiunas2, Lukas Naimovičius2, Karolis Kazlauskas2, Edvinas Orentas1

1 Department of Organic Chemistry, Faculty of Chemistry and Geosciences, Vilnius University, Lithuania

2 Institute of Photonics and Nanotechnology, Faculty of Physics, Vilnius University, Lithuania

[email protected]

Triplet fusion (TF) upconversion is a process allowing the conversion of two or more low-energy photons to one high-energy photon. Light upconverting systems have great implications in many fields, such as photovoltaics, photocatalysis or bioimaging. Despite a large demand, the choice of efficient organic materials is rather limiting, especially for the most practically relevant NIR to visible upconversion [1-2]. TF upconversion requires two types of molecules, a sensitizer and an annihilator, the latter often being the limiting component. To extend the collection of possible emitters and to gain fundamental insights into upconversion process itself our team sought to develop new derivatives of diketopyrrolopyrrole (DPP), a commonly used dye in organic optoelectronics.

DPP has been widely explored in the field of organic photovoltaics because of its excellent optical properties, such as strong absorption in the visible range and high fluorescence quantum yield [3]. In order to apply DPPs in upconversion devices, their high aggregation propensity, detrimental to fluorescence, has to be attenuated by structural design. To this end we have designed, synthesized and evaluated new alkyl chain strapped sterically hindered DPP derivative 1 (Fig. 1). The successful modulation of aggregation process is expected to provide a working material not only for solution but also for more difficult to achieve upconversion in films.

Figure 1
Fig. 1. Chemical structure of macrocyclic DPP derivative.

Acknowledgments: This project has received funding from the European Regional Development Fund (Project No. 09.3.3-LMT-K712-22-0191) under grant agreement with the Research Council of Lithuania (LMTLT)


[1] J. Zhou, Q. Liu, W. Feng et al., Upconversion luminescent materials: advances and applications, Chemical Reviews 115, 395-465 (2015).

[2] S. Wen, J. Zhou, J. Schuck et al., Future and challenges for hybrid upconversion nanosystems, Nature Photonics 13, 828-838 (2019).

[3] A. B. Pun, L. M. Campos, D. N. Congreve., Tunable Emission from Triplet Fusion Upconversion in Diketopyrrolopyrroles, J. Am. Chem. Soc. 141, 9,3777-3781 (2019).