Abstract
A new family of naphthalimide-fused thienopyrazine derivatives for ambipolar charge transport in organic field-effect transistors is presented. Their electronic and molecular structures were elucidated through optical and vibrational spectroscopy aided by DFT calculations. The results indicate that these compounds have completely planar molecular skeletons which promote good film crystallinity and low reorganization energies for both electron and hole transport. Their performance in organic field-effect transistors is compared with twisted and planar naphthaleneamidine monoimide-fused terthiophenes in order to understand the origin of ambipolarity in this new series of molecular semiconductors. Tailoring ambipolarity: A new family of completely planar naphthalimide-fused thienopyrazine derivatives in which coplanarity is enforced by intramolecular S×××N interactions has been synthesized for ambipolar charge transport in organic field-effect transistors and analyzed by vibrational spectroscopy and DFT calculations. Their data are compared with those previously reported for a series of planar and twisted thiophene-naphthalene derivatives (see figure) and afford new understanding of OFET performance in this general class of molecular semiconductors.
| Original language | English |
|---|---|
| Pages (from-to) | 12458-12467 |
| Number of pages | 10 |
| Journal | Chemistry - A European Journal |
| Volume | 19 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - Sep 9 2013 |
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Keywords
- ambipolarity
- density functional calculations
- molecular electronics
- semiconductors
- thin films
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Molecular and electronic-structure basis of the ambipolar behavior of naphthalimide-terthiophene derivatives : Implementation in organic field-effect transistors. / Ponce Ortiz, Rocío; Herrera, Helena; Mancheño, María J.; Seoane, Carlos; Segura, José L.; Mayorga Burrezo, Paula; Casado, Juan; Lõpez Navarrete, J. Teodomiro; Facchetti, Antonio; Marks, Tobin J.
In: Chemistry - A European Journal, Vol. 19, No. 37, 09.09.2013, p. 12458-12467.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Molecular and electronic-structure basis of the ambipolar behavior of naphthalimide-terthiophene derivatives
T2 - Implementation in organic field-effect transistors
AU - Ponce Ortiz, Rocío
AU - Herrera, Helena
AU - Mancheño, María J.
AU - Seoane, Carlos
AU - Segura, José L.
AU - Mayorga Burrezo, Paula
AU - Casado, Juan
AU - Lõpez Navarrete, J. Teodomiro
AU - Facchetti, Antonio
AU - Marks, Tobin J
PY - 2013/9/9
Y1 - 2013/9/9
N2 - A new family of naphthalimide-fused thienopyrazine derivatives for ambipolar charge transport in organic field-effect transistors is presented. Their electronic and molecular structures were elucidated through optical and vibrational spectroscopy aided by DFT calculations. The results indicate that these compounds have completely planar molecular skeletons which promote good film crystallinity and low reorganization energies for both electron and hole transport. Their performance in organic field-effect transistors is compared with twisted and planar naphthaleneamidine monoimide-fused terthiophenes in order to understand the origin of ambipolarity in this new series of molecular semiconductors. Tailoring ambipolarity: A new family of completely planar naphthalimide-fused thienopyrazine derivatives in which coplanarity is enforced by intramolecular S×××N interactions has been synthesized for ambipolar charge transport in organic field-effect transistors and analyzed by vibrational spectroscopy and DFT calculations. Their data are compared with those previously reported for a series of planar and twisted thiophene-naphthalene derivatives (see figure) and afford new understanding of OFET performance in this general class of molecular semiconductors.
AB - A new family of naphthalimide-fused thienopyrazine derivatives for ambipolar charge transport in organic field-effect transistors is presented. Their electronic and molecular structures were elucidated through optical and vibrational spectroscopy aided by DFT calculations. The results indicate that these compounds have completely planar molecular skeletons which promote good film crystallinity and low reorganization energies for both electron and hole transport. Their performance in organic field-effect transistors is compared with twisted and planar naphthaleneamidine monoimide-fused terthiophenes in order to understand the origin of ambipolarity in this new series of molecular semiconductors. Tailoring ambipolarity: A new family of completely planar naphthalimide-fused thienopyrazine derivatives in which coplanarity is enforced by intramolecular S×××N interactions has been synthesized for ambipolar charge transport in organic field-effect transistors and analyzed by vibrational spectroscopy and DFT calculations. Their data are compared with those previously reported for a series of planar and twisted thiophene-naphthalene derivatives (see figure) and afford new understanding of OFET performance in this general class of molecular semiconductors.
KW - ambipolarity
KW - density functional calculations
KW - molecular electronics
KW - semiconductors
KW - thin films
UR - http://www.scopus.com/inward/record.url?scp=84883457847&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84883457847&partnerID=8YFLogxK
U2 - 10.1002/chem.201301489
DO - 10.1002/chem.201301489
M3 - Article
VL - 19
SP - 12458
EP - 12467
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 37
ER -