Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes

Shao Ling Chang; Chih Wen Lu; Yu Ying Lai; Jhih Yang Hsu; Yen-Ju Cheng

doi:10.1021/acs.orglett.5b03294

Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes

Shao Ling Chang, Chih Wen Lu, Yu Ying Lai, Jhih Yang Hsu, Yen-Ju Cheng^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article

8 Scopus citations

Abstract

Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl ₂ -catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10 ^-2 cm ² V ^-1 s ^-1 .

Original language	English
Pages (from-to)	368-371
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.5b03294
State	Published - 5 Feb 2016

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Chang, S. L., Lu, C. W., Lai, Y. Y., Hsu, J. Y., & Cheng, Y-J. (2016). Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes. Organic Letters, 18(3), 368-371. https://doi.org/10.1021/acs.orglett.5b03294

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title = "Synthesis and molecular properties of two isomeric dialkylated tetrathienonaphthalenes",

abstract = " Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl 2 -catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10 -2 cm 2 V -1 s -1 . ",

author = "Chang, {Shao Ling} and Lu, {Chih Wen} and Lai, {Yu Ying} and Hsu, {Jhih Yang} and Yen-Ju Cheng",

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doi = "10.1021/acs.orglett.5b03294",

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AU - Chang, Shao Ling

AU - Lu, Chih Wen

AU - Lai, Yu Ying

AU - Hsu, Jhih Yang

AU - Cheng, Yen-Ju

PY - 2016/2/5

Y1 - 2016/2/5

N2 - Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl 2 -catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10 -2 cm 2 V -1 s -1 .

AB - Isomeric 2,8-distannyl 5,11-didodecyl αβ-TTN (1, tetrathienonaphthalene = TTN) and 2,8-didodecyl 5,11-distannyl αβ-TTN (2) have been designed and successfully synthesized. The naphthalene core structures in αβ-TTNs were constructed by a systematic protocol using PtCl 2 -catalyzed cyclization followed by oxidative Scholl annulation in good yields. Compared to the one-dimensional naphthodithiophene derivatives, the two-dimensional αβ-TTN molecules showed good solubility, extended conjugation, strong absorptivity, and highly coplanar structures. Compounds 1 and 2 were polymerized with a 5,5′-dibromo-2,2′-bithiophene-based monomer to afford 2,8-αβ-PTTNTT and 5,11-αβ-PTTNTT copolymers. 2,8-αβ-PTTNTT with the α-aNDT moiety in the main chain exhibited a higher hole mobility of 1.26 × 10 -2 cm 2 V -1 s -1 .

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