DOI: 10.1002/chem.201101715. Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene

Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene–Naphthalene Semiconductors?

10.1002/chem.201101715

Crossref journal-article

Wiley

Chemistry – A European Journal (311)

Abstract

AbstractHerein, we report a new family of naphthaleneamidinemonoimide‐fused oligothiophene semiconductors designed for facile charge transport in organic field‐effect transistors (OFETs). These molecules have planar skeletons that induce high degrees of crystallinity and hence good charge‐transport properties. By modulating the length of the oligothiophene fragment, the majority carrier charge transport can be switched from n‐type to ambipolar behavior. The highest FET performance is achieved for solution‐processed films of 10‐[(2,2′‐bithiophen)‐5‐yl]‐2‐octylbenzo[lmn]thieno[3′,4′:4,5]imidazo[2,1‐b][3,8]phenanthroline‐1,3,6(2 H)‐trione (NDI‐3 Tp), with optimized film mobilities of 2×10−2 and 0.7×10−2 cm2 V−1 s−1 for electrons and holes, respectively. Finally, these planar semiconductors are compared with their twisted‐skeleton counterparts, which exhibit only n‐type mobility, in order to understand the origin of the ambipolarity in this new series of molecular semiconductors.

Bibliography

Ortiz, R. P., Herrera, H., Seoane, C., Segura, J. L., Facchetti, A., & Marks, T. J. (2011). Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in ThiopheneâNaphthalene Semiconductors? Chemistry â A European Journal, 18(2), 532â543. Portico.

Authors 6

Rocío Ponce Ortiz (first)
Helena Herrera (additional)
Carlos Seoane (additional)
José L. Segura (additional)
Antonio Facchetti (additional)
Tobin J. Marks (additional)

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Dates

Type	When
Created	13 years, 8 months ago (Dec. 12, 2011, 8:45 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 1:06 p.m.)
Indexed	2 months ago (July 2, 2025, 3:53 a.m.)
Issued	13 years, 8 months ago (Dec. 12, 2011)
Published	13 years, 8 months ago (Dec. 12, 2011)
Published Online	13 years, 8 months ago (Dec. 12, 2011)
Published Print	13 years, 7 months ago (Jan. 9, 2012)

Funders 0

None

BibTeX

@article{Ortiz_2011, title={Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene–Naphthalene Semiconductors?}, volume={18}, ISSN={1521-3765}, url={http://dx.doi.org/10.1002/chem.201101715}, DOI={10.1002/chem.201101715}, number={2}, journal={Chemistry – A European Journal}, publisher={Wiley}, author={Ortiz, Rocío Ponce and Herrera, Helena and Seoane, Carlos and Segura, José L. and Facchetti, Antonio and Marks, Tobin J.}, year={2011}, month=dec, pages={532–543} }

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