Phthalimides and naphthalimides fused with diaminonaphthalene as novel blocks building conjugated polymers for optoelectronics applications

Malgorzata Czichy^a, Pawel Zassowski^a, Aleksandra Wolinska-Grabczyk^b, Mieczyslaw Lapkowski^a^,^b

^aFaculty of Chemistry, Silesian University of Technology, M. Strzody 9, 44-100 Gliwice, Poland

^bCentre of Polymer and Carbon Materials, Polish Academy of Sciences, Zabrze, Poland, 34 Marie Curie-Sklodowska Str, Zabrze, Poland

International Conference on Hybrid and Organic Photovoltaics
Proceedings of International Conference on Hybrid and Organic Photovoltaics (HOPV18)

Benidorm, Spain, 2018 May 28th - 31st

Organizers: Emilio Palomares and Rene Janssen

Poster, Malgorzata Czichy, 287
Publication date: 21st February 2018

In the past years have seen a surge of interest of new ambipolar copolymers containing polycyclic aromatic hydrocarbons segments as acceptors. Modified arylene bisimides with various electron-donating groups leads to significant changes in their electronic structure and can be useful in devices such as light-emitting diodes, organic thin-film transistors (OTFTs), organic photovoltaics (OPVs), organic electronics and organic field effect transistors (OFET).

The most commonly bonds connecting donor unit with e.g. naphthalene or perylene are acetic anhydride (e.g. perylenetetracarboxylic dianhydride) and formylformamide (substituted perylenedicarboximide [1]). The structure of the last example allows donor addition (e.g. thiophene, triphenylamines) through nitrogen fixation. This type of molecules could be polymerized chemically or electrochemically giving a polymers with a better conductivity than small molecules. Interesting solution is fusing five-membered ring e.g. 1H-imidazole-1-carbaldehyde unit as in case of poly(benzobisimidazobenzophenanthrolines) (BBB, BBL) presented in the literature [2,3,4]. In turn, we propose the synthesis of a new types of annulated aromatic dianhydrides by using of 1,8-naphthalenediamide.

Phthalimides and naphthalimides after fusing with naphthalenediamid were subjected electropolarization to induced (in a controlled manner) subsequent oxidation or reduction stages. Electroreduction leads to production of stable radical anions. In turn, radical cations and diradical dications are reactive, so π-conjugated polymer are produces with naphthalimides-diaminonaphthalene precursors. The nodes of the created polymers networks are conjugated what provides free flow of electric charges. Obtained products are characterized by a high air, thermal and photochemical stability, and low band gap values. This will allow its applications as electrodes in organic electronics, and as the main active material in polymeric batteries or supercapacitors.

References:

1. Kew-Yu Chen, Che-Wei Chang, Hsing-Yang Tsai, Materials 2015, 8(8), 4943-4960

2. Amit Babel, Yan Zhu, Kai-Fang Cheng, Wen-Chang Chen, Samson A. Jenekhe, Adv. Funct. Mater. 2007, 17, 2542–2549

3. X. Linda Chen and Samson A. Jenekhe, Macromolecules 1997, 30, 1728-1733

Amit Babel and Samson A. Jenekhe, J. Phys. Chem. B, 2002, 106( 24),6129- 6132

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