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Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units

We demonstrate a new method to reverse the polarity and charge transport behavior of naphthalenediimide (NDI)-based copolymers by inserting a vinylene linker between the donor and acceptor units. The vinylene linkers minimize the intrinsic steric congestion between the NDI and thiophene moieties to...

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Published in:Chemistry of materials 2016-12, Vol.28 (23), p.8580-8590
Main Authors: Zhang, Lei, Rose, Bradley D, Liu, Yao, Nahid, Masrur M, Gann, Eliot, Ly, Jack, Zhao, Wei, Rosa, Stephen J, Russell, Thomas P, Facchetti, Antonio, McNeill, Christopher R, Brédas, Jean-Luc, Briseno, Alejandro L
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cited_by cdi_FETCH-LOGICAL-a295t-53ae093f5b9d38c20228c1b345f555322ddd70ae8dab2a00f62913c086ec3a8a3
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container_end_page 8590
container_issue 23
container_start_page 8580
container_title Chemistry of materials
container_volume 28
creator Zhang, Lei
Rose, Bradley D
Liu, Yao
Nahid, Masrur M
Gann, Eliot
Ly, Jack
Zhao, Wei
Rosa, Stephen J
Russell, Thomas P
Facchetti, Antonio
McNeill, Christopher R
Brédas, Jean-Luc
Briseno, Alejandro L
description We demonstrate a new method to reverse the polarity and charge transport behavior of naphthalenediimide (NDI)-based copolymers by inserting a vinylene linker between the donor and acceptor units. The vinylene linkers minimize the intrinsic steric congestion between the NDI and thiophene moieties to prompt backbone planarity. The polymers with vinylene linkers exhibit electron n-channel transport characteristics under vacuum, similar to the benchmark polymer, P­(NDI2OD-T2). To our surprise, when the polymers are measured in air, the dominant carrier type switches from n- to p-type and yield hole mobilities up to 0.45 cm2 V–1 s–1 with hole to electron mobility ratio of three (μh/μe, ∼3), which indicates that the hole density in the active layer can be significantly increased by exposure to air. This increase is consistent with the intrinsic more delocalized nature of the highest occupied molecular orbital of the charged vinylene polymer, as estimated by density functional theory (DFT) calculations, which facilitates hole transport within the polymer chains. This is the first demonstration of an efficient NDI-based hole semiconducting polymer, which will enable new developments in all-polymer solar cells, complementary circuits, and dopable polymers for use in thermoelectrics.
doi_str_mv 10.1021/acs.chemmater.6b03379
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title Efficient Naphthalenediimide-Based Hole Semiconducting Polymer with Vinylene Linkers between Donor and Acceptor Units
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