TY - JOUR
T1 - Effect of Backbone Regiochemistry on Conductivity, Charge Density, and Polaron Structure of n-Doped Donor-Acceptor Polymers
AU - Wang, Suhao
AU - Fazzi, Daniele
AU - Puttisong, Yuttapoom
AU - Jafari, Mohammad J.
AU - Chen, Zhihua
AU - Ederth, Thomas
AU - Andreasen, Jens W.
AU - Chen, Weimin M.
AU - Facchetti, Antonio
AU - Fabiano, Simone
N1 - Funding Information:
The authors acknowledge the support from the Knut and Alice Wallenberg foundation, the Swedish Foundation for Strategic Research. S.F. gratefully acknowledges funding by VINNOVA (2015-04859), the Swedish Research Council (2016-03979), the Advanced Functional Materials Center at Linköping University (2009-00971), and ÅForsk (18-313). A.F. thanks AFOSR (FA9550-18-1-0320). D.F. acknowledges the Deutsche Forschungsgemeinschaft (DFG) for a Principal Investigator grant (FA 1502/1-1 “Molecular Understanding of Thermo-Electric Properties in Organic Polymers”). J.W.A. gratefully acknowledges funding by the European Research Council (ERC) (681881).
Funding Information:
The authors acknowledge the support from the Knut and Alice Wallenberg foundation, the Swedish Foundation for Strategic Research. S.F. gratefully acknowledges funding by VINNOVA (2015-04859), the Swedish Research Council (2016-03979), the Advanced Functional Materials Center at Linko?ping University (2009-00971), and ÅForsk (18-313). A.F. thanks AFOSR (FA9550-18-1-0320). D.F. acknowledges the Deutsche Forschungsgemeinschaft (DFG) for a Principal Investigator grant (FA 1502/1-1 "Molecular Understanding of Thermo-Electric Properties in Organic Polymers"). J.W.A. gratefully acknowledges funding by the European Research Council (ERC) (681881).
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/5/14
Y1 - 2019/5/14
N2 - We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor-acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV-vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor-acceptor polymers.
AB - We investigated the influence of backbone regiochemistry on the conductivity, charge density, and polaron structure in the widely studied n-doped donor-acceptor polymer poly[N,N′-bis(2-octyldodecyl)-1,4,5,8-naphthalenediimide-2,6-diyl]-alt-5,5′-(2,2′-bithiophene) [P(NDI2OD-T2)]. In contrast to classic semicrystalline polymers such as poly(3-hexylthiophene) (P3HT), the regioirregular (RI) structure of the naphthalenediimide (NDI)-bithiophene (T2) backbone does not alter the intramolecular steric demand of the chain versus the regioregular (RR) polymer, yielding RI-P(NDI2OD-T2) with similar energetics and optical features as its RR counterpart. By combining the electrical, UV-vis/infrared, X-ray diffraction, and electron paramagnetic resonance data and density functional theory calculations, we quantitatively characterized the conductivity, aggregation, crystallinity, and charge density, and simulated the polaron structures, molecular vibrations, and spin density distribution of RR-/RI-P(NDI2OD-T2). Importantly, we observed that RI-P(NDI2OD-T2) can be doped to a greater extent compared to its RR counterpart. This finding is remarkable and contrasts benchmark P3HT, allowing us to uniquely study the role of regiochemistry on the charge-transport properties of n-doped donor-acceptor polymers.
UR - http://www.scopus.com/inward/record.url?scp=85065728038&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85065728038&partnerID=8YFLogxK
U2 - 10.1021/acs.chemmater.9b00558
DO - 10.1021/acs.chemmater.9b00558
M3 - Article
C2 - 31296974
AN - SCOPUS:85065728038
SN - 0897-4756
VL - 31
SP - 3395
EP - 3406
JO - Chemistry of Materials
JF - Chemistry of Materials
IS - 9
ER -