Abstract
We report a new naphthalene bis(4,8-diamino-1,5-dicarboxyl)amide (NBA) building block for polymeric semiconductors. Computational modeling suggests that regio-connectivity at the 2,6- or 3,7-NBA positions strongly modulates polymer backbone torsion and, therefore, intramolecular π-conjugation and aggregation. Optical, electrochemical, and X-ray diffraction characterization of 3,7- and 2,6-dithienyl-substituted NBA molecules and corresponding isomeric NBA-bithiophene copolymers P1 and P2, respectively, reveals the key role of regio-connectivity. Charge transport measurements demonstrate that while the twisted 3,7-NDA-based P1 is a poor semiconductor, the planar 2,6-functionalized NBA polymers (P2-P4) exhibit ambipolarity, with μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively.
Original language | English (US) |
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Pages (from-to) | 14356-14359 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 139 |
Issue number | 41 |
DOIs | |
State | Published - Oct 18 2017 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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CCDC 1576724: Experimental Crystal Structure Determination
Eckstein, B. J. (Creator), Melkonyan, F. S. (Creator), Manley, E. F. (Creator), Fabiano, S. (Creator), Mouat, A. R. (Creator), Chen, L. X. (Creator), Facchetti, A. F. (Creator) & Marks, T. J. (Creator), Cambridge Crystallographic Data Centre, 2017
DOI: 10.5517/ccdc.csd.cc1pxq2d, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pxq2d&sid=DataCite
Dataset
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CCDC 1576725: Experimental Crystal Structure Determination
Eckstein, B. J. (Creator), Melkonyan, F. S. (Creator), Manley, E. F. (Creator), Fabiano, S. (Creator), Mouat, A. R. (Creator), Chen, L. X. (Creator), Facchetti, A. F. (Creator) & Marks, T. J. (Creator), Cambridge Crystallographic Data Centre, 2017
DOI: 10.5517/ccdc.csd.cc1pxq3f, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pxq3f&sid=DataCite
Dataset