π-Extended perylene diimide double-heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection

ARTICLE π-Extended perylene diimide double- heterohelicenes as ambipolar organic semiconductors for broadband circularly polarized light detection Li Zhang1,6, Inho Song2,6, Jaeyong Ahn2, Myeonggeun Han3, Mathieu Linares 4, Mathieu Surin 5, Hui-Jun Zhang 1, Joon Hak Oh 2✉& Jianbin Lin 1✉ Despite great challenges, the development of new molecular structures with multiple and even conflicting characteristics are eagerly pursued for exploring advanced applications. To develop high-performance chiral organic semiconducting molecules, a distorted π-system is required for strong coupling with circularly polarized light (CPL), whereas planar π-stacking systems are necessary for high charge-carrier mobility. To address this dilemma, in this work, we introduce a skeleton merging approach through distortion of a perylene diimide (PDI) core with four fused heteroaromatics to form an ortho-π-extended PDI double-[7]hetero- helicene. PDI double helicene inherits a high dissymmetry factor from the helicene skeleton, and the extended π-planar system concurrently maintains a high level of charge transport properties. In addition, ortho-π-extension of the PDI skeleton brings about near-infrared (NIR) light absorption and ambipolar charge transport abilities, endowing the corresponding organic phototransistors with high photoresponsivity of 450 and 120 mA W−1 in p- and n-type modes respectively, along with a high external quantum efficiency (89%) under NIR light irradia- tions. Remarkably, these multiple characteristics enable high-performance broadband CPL detections up to NIR spectral region with chiral organic semiconductors. https://doi.org/10.1038/s41467-020-20390-y OPEN 1 Department of Chemistry, College of Chemistry and Chemical Engineering, MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Xiamen University, Xiamen 361005, China. 2 School of Chemical and Biological Engineering, Institute of Chemical Processes, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. 3 Department of Chemical Engineering, Pohang University of Science and Technology (POSTECH), Gyeongbuk, Pohang 37673, Korea. 4 Laboratory of Organic Electronics and Scientific Visualization Group, ITN, Campus Norrköping; Swedish e-Science Research Centre (SeRC), Linköping University, Linköping SE-581 83, Sweden. 5 Laboratory for Chemistry of Novel Materials, Centre of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons – UMONS, 20 Place du Parc, Mons B-7000, Belgium. 6These authors contributed equally: Li Zhang, Inho Song. ✉email: joonhoh@snu.ac.kr; jb.lin@xmu.edu.cn NATURE COMMUNICATIONS | (2021) 12:142 | https://doi.org/10.1038/s41467-020-20390-y | www.nature.com/naturecommunications 1 123