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 |
|---|---|
| Pages (from-to) | 14356-14359 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 139 |
| Issue number | 41 |
| DOIs | |
| Publication status | Published - Oct 18 2017 |
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ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers. / Eckstein, Brian J.; Melkonyan, Ferdinand S.; Manley, Eric F.; Fabiano, Simone; Mouat, Aidan R.; Chen, Lin X.; Facchetti, Antonio; Marks, Tobin J.
In: Journal of the American Chemical Society, Vol. 139, No. 41, 18.10.2017, p. 14356-14359.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers
AU - Eckstein, Brian J.
AU - Melkonyan, Ferdinand S.
AU - Manley, Eric F.
AU - Fabiano, Simone
AU - Mouat, Aidan R.
AU - Chen, Lin X.
AU - Facchetti, Antonio
AU - Marks, Tobin J
PY - 2017/10/18
Y1 - 2017/10/18
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=85031758979&partnerID=8YFLogxK
U2 - 10.1021/jacs.7b07750
DO - 10.1021/jacs.7b07750
M3 - Article
VL - 139
SP - 14356
EP - 14359
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 41
ER -