PMID- 34850459
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20220602
IS  - 1521-4095 (Electronic)
IS  - 0935-9648 (Linking)
VI  - 34
IP  - 22
DP  - 2022 Jun
TI  - Controlled n-Doping of Naphthalene-Diimide-Based 2D Polymers.
PG  - e2101932
LID - 10.1002/adma.202101932 [doi]
AB  - 2D polymers (2DPs) are promising as structurally well-defined, permanently 
      porous, organic semiconductors. However, 2DPs are nearly always isolated as 
      closed shell organic species with limited charge carriers, which leads to low 
      bulk conductivities. Here, the bulk conductivity of two naphthalene diimide 
      (NDI)-containing 2DP semiconductors is enhanced by controllably n-doping the NDI 
      units using cobaltocene (CoCp(2) ). Optical and transient microwave spectroscopy 
      reveal that both as-prepared NDI-containing 2DPs are semiconducting with sub-2 eV 
      optical bandgaps and photoexcited charge-carrier lifetimes of tens of 
      nanoseconds. Following reduction with CoCp(2) , both 2DPs largely retain their 
      periodic structures and exhibit optical and electron-spin resonance spectroscopic 
      features consistent with the presence of NDI-radical anions. While the native 
      NDI-based 2DPs are electronically insulating, maximum bulk conductivities of 
      >10(-4 ) S cm(-1) are achieved by substoichiometric levels of n-doping. Density 
      functional theory calculations show that the strongest electronic couplings in 
      these 2DPs exist in the out-of-plane (pi-stacking) crystallographic directions, 
      which indicates that cross-plane electronic transport through NDI stacks is 
      primarily responsible for the observed electronic conductivity. Taken together, 
      the controlled molecular doping is a useful approach to access structurally 
      well-defined, paramagnetic, 2DP n-type semiconductors with measurable bulk 
      electronic conductivities of interest for electronic or spintronic devices.
CI  - (c) 2022 Wiley-VCH GmbH.
FAU - Evans, Austin M
AU  - Evans AM
AUID- ORCID: 0000-0002-3597-2454
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Collins, Kelsey A
AU  - Collins KA
AUID- ORCID: 0000-0002-9202-8179
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Xun, Sangni
AU  - Xun S
AD  - School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, 
      GA, 30332, USA.
AD  - Center for Organic Photonics and Electronics, Georgia Institute of Technology, 
      Atlanta, GA, 30332, USA.
AD  - College of Environmental Science and Engineering, Hunan University, Changsha, 
      410082, P. R. China.
FAU - Allen, Taylor G
AU  - Allen TG
AUID- ORCID: 0000-0003-0829-4165
AD  - Center for Chemistry and Nanoscience, National Renewable Energy Laboratory, 15013 
      Denver West Parkway, Golden, CO, 80401, USA.
FAU - Jhulki, Samik
AU  - Jhulki S
AUID- ORCID: 0000-0003-1318-8666
AD  - School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, 
      GA, 30332, USA.
AD  - Center for Organic Photonics and Electronics, Georgia Institute of Technology, 
      Atlanta, GA, 30332, USA.
FAU - Castano, Ioannina
AU  - Castano I
AUID- ORCID: 0000-0001-6491-2170
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Smith, Hannah L
AU  - Smith HL
AUID- ORCID: 0000-0002-7290-8865
AD  - Department of Electrical and Computer Engineering, Princeton University, 
      Princeton, NJ, 08544, USA.
FAU - Strauss, Michael J
AU  - Strauss MJ
AUID- ORCID: 0000-0003-0808-2568
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Oanta, Alexander K
AU  - Oanta AK
AUID- ORCID: 0000-0002-3188-2240
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Liu, Lujia
AU  - Liu L
AUID- ORCID: 0000-0001-9452-4371
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
FAU - Sun, Lei
AU  - Sun L
AUID- ORCID: 0000-0001-8467-6750
AD  - Center for Nanoscale Materials, Argonne National Laboratory, Lemont, IL, 60439, 
      USA.
FAU - Reid, Obadiah G
AU  - Reid OG
AUID- ORCID: 0000-0003-0646-3981
AD  - Center for Chemistry and Nanoscience, National Renewable Energy Laboratory, 15013 
      Denver West Parkway, Golden, CO, 80401, USA.
AD  - Renewable and Sustainable Energy Institute, Department of Chemistry, University 
      of Colorado Boulder, Boulder, CO, 80309, USA.
FAU - Sini, Gjergji
AU  - Sini G
AUID- ORCID: 0000-0003-2548-8260
AD  - Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ, 
      85721, USA.
AD  - CY Cergy Paris Universite, Laboratoire de Physicochimie des Polymeres et des 
      Interfaces, EA 2528, 5 mail Gay-Lussac, Cergy-Pontoise Cedex, 95031, France.
FAU - Puggioni, Danilo
AU  - Puggioni D
AUID- ORCID: 0000-0002-2128-4191
AD  - Department of Materials Science and Engineering, Northwestern University, 
      Evanston, IL, 60208, USA.
FAU - Rondinelli, James M
AU  - Rondinelli JM
AUID- ORCID: 0000-0003-0508-2175
AD  - Department of Materials Science and Engineering, Northwestern University, 
      Evanston, IL, 60208, USA.
FAU - Rajh, Tijana
AU  - Rajh T
AUID- ORCID: 0000-0003-2218-4130
AD  - Center for Nanoscale Materials, Argonne National Laboratory, Lemont, IL, 60439, 
      USA.
FAU - Gianneschi, Nathan C
AU  - Gianneschi NC
AUID- ORCID: 0000-0001-9945-5475
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
AD  - Department of Materials Science and Engineering, Northwestern University, 
      Evanston, IL, 60208, USA.
AD  - International Institute for Nanotechnology, Department of Biomedical Engineering, 
      Department of Pharmacology, Simpson Querrey Institute, and Chemistry of Life 
      Processes Institute, Evanston, IL, 60208, USA.
FAU - Kahn, Antoine
AU  - Kahn A
AUID- ORCID: 0000-0002-1612-3350
AD  - Department of Electrical and Computer Engineering, Princeton University, 
      Princeton, NJ, 08544, USA.
FAU - Freedman, Danna E
AU  - Freedman DE
AUID- ORCID: 0000-0002-2579-8835
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
AD  - Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, 
      02139, USA.
FAU - Li, Hong
AU  - Li H
AD  - Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ, 
      85721, USA.
FAU - Barlow, Stephen
AU  - Barlow S
AUID- ORCID: 0000-0001-9059-9974
AD  - School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, 
      GA, 30332, USA.
AD  - Center for Organic Photonics and Electronics, Georgia Institute of Technology, 
      Atlanta, GA, 30332, USA.
FAU - Rumbles, Garry
AU  - Rumbles G
AUID- ORCID: 0000-0003-0776-1462
AD  - Center for Chemistry and Nanoscience, National Renewable Energy Laboratory, 15013 
      Denver West Parkway, Golden, CO, 80401, USA.
AD  - Renewable and Sustainable Energy Institute, Department of Chemistry, University 
      of Colorado Boulder, Boulder, CO, 80309, USA.
FAU - Bredas, Jean-Luc
AU  - Bredas JL
AUID- ORCID: 0000-0001-7278-4471
AD  - Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ, 
      85721, USA.
FAU - Marder, Seth R
AU  - Marder SR
AUID- ORCID: 0000-0001-6921-2536
AD  - School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, 
      GA, 30332, USA.
AD  - Center for Organic Photonics and Electronics, Georgia Institute of Technology, 
      Atlanta, GA, 30332, USA.
FAU - Dichtel, William R
AU  - Dichtel WR
AUID- ORCID: 0000-0002-3635-6119
AD  - Department of Chemistry, Northwestern University, Evanston, IL, 60208, USA.
LA  - eng
GR  - W911NF-15-1-0447/Multidisciplinary University Research Initiatives/
GR  - DE-SC0019356/Department of Energy/
GR  - DGE-1324585/Department of Energy/
GR  - DGE-1842165/Department of Energy/
GR  - DGE-11842165/Department of Energy/
GR  - National Science Foundation/
GR  - United States-India Educational Foundation/
GR  - 2266/FNPDR/2017/Institute of International Education/
GR  - DMR-1807797/National Science Foundation/
GR  - DGE-1656466/National Science Foundation/
GR  - NNCI-1542205/Soft and Hybrid Nanotechnology Experimental (SHyNE)/
GR  - ECCS1542205/Soft and Hybrid Nanotechnology Experimental (SHyNE)/
GR  - DMR-1720139/National Science Foundation/
GR  - State of Illinois, and the International Institute for Nanotechnology/
GR  - U.S. Department of Energy/
GR  - DE-AC02-06CH11357/Argonne National Laboratory/
GR  - National Energy Research Scientific Computing Center/
GR  - DE-AC02-05CH11231/U.S. Department of Energy/
GR  - 0960140/National Science Foundation/
GR  - DE-AC36-08GO28308/U.S. Department of Energy/
PT  - Journal Article
DEP - 20220208
PL  - Germany
TA  - Adv Mater
JT  - Advanced materials (Deerfield Beach, Fla.)
JID - 9885358
SB  - IM
OTO - NOTNLM
OT  - 2D polymers
OT  - conductive polymers
OT  - n-type molecular doping
OT  - organic semiconductors
EDAT- 2021/12/02 06:00
MHDA- 2021/12/02 06:01
CRDT- 2021/12/01 07:41
PHST- 2021/11/12 00:00 [revised]
PHST- 2021/03/10 00:00 [received]
PHST- 2021/12/02 06:00 [pubmed]
PHST- 2021/12/02 06:01 [medline]
PHST- 2021/12/01 07:41 [entrez]
AID - 10.1002/adma.202101932 [doi]
PST - ppublish
SO  - Adv Mater. 2022 Jun;34(22):e2101932. doi: 10.1002/adma.202101932. Epub 2022 Feb 
      8.