Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state

Kun Yang; Xiang Li; Yi Fan Huang; Ram S. Bhatta; Jiawei Liu; Mesfin Tsige; Chien-Lung Wang; Stephen Z.D. Cheng; Yu Zhu

doi:10.1016/j.polymer.2018.11.029

Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state

Kun Yang, Xiang Li, Yi Fan Huang, Ram S. Bhatta, Jiawei Liu, Mesfin Tsige, Chien-Lung Wang, Stephen Z.D. Cheng, Yu Zhu^*

^*Corresponding author for this work

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.

Original language	English
Pages (from-to)	238-245
Number of pages	8
Journal	polymer
Volume	160
DOIs	https://doi.org/10.1016/j.polymer.2018.11.029
State	Published - 3 Jan 2019

Keywords

Conjugated molecules
Hydrogen bond
Molecular packing

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10.1016/j.polymer.2018.11.029

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@article{5635d1e551e54e7fb4c05b077363a980,

title = "Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state",

abstract = "Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.",

keywords = "Conjugated molecules, Hydrogen bond, Molecular packing",

author = "Kun Yang and Xiang Li and Huang, {Yi Fan} and Bhatta, {Ram S.} and Jiawei Liu and Mesfin Tsige and Chien-Lung Wang and Cheng, {Stephen Z.D.} and Yu Zhu",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2019",

month = jan,

day = "3",

doi = "10.1016/j.polymer.2018.11.029",

language = "English",

volume = "160",

pages = "238--245",

journal = "polymer",

issn = "0032-3861",

publisher = "Elsevier B.V.",

}

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T1 - Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state

AU - Yang, Kun

AU - Li, Xiang

AU - Huang, Yi Fan

AU - Bhatta, Ram S.

AU - Liu, Jiawei

AU - Tsige, Mesfin

AU - Wang, Chien-Lung

AU - Cheng, Stephen Z.D.

AU - Zhu, Yu

PY - 2019/1/3

Y1 - 2019/1/3

N2 - Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.

AB - Two diketopyrrolopyrrole (DPP)-based donor-acceptor oligomers with thermal labile 2-methylhexyl-2-oxylcarbonyl (mHoc) groups, mHocPBT and mHocTBT, were synthesized and characterized to study the hydrogen-bonding mediated molecular packing in solid state. The soluble oligomers can be converted to strong intermolecular hydrogen-bonded and pigment-like materials HPBT and HTBT by annealing the casted solid film at a temperature between 180 and 200 °C. The formation of intermolecular hydrogen bonding significantly altered the conformation of the molecules, molecular packing structure and related optical properties of the oligomers, with HPBT molecule exhibiting bathochromic shift and HTBT molecule exhibiting hypsochromic shift on UV/Vis spectra. Spin-casted mHocTBT and HTBT films also exhibited interesting morphology and charge transport properties. Even though the single mHocTBT oligomer molecule has a better coplanar molecular conformation as compared with that of HTBT, an enhanced π-π stacking structure and larger crystal grain size rendered HTBT film better charge transport performance.

KW - Conjugated molecules

KW - Hydrogen bond

KW - Molecular packing

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U2 - 10.1016/j.polymer.2018.11.029

DO - 10.1016/j.polymer.2018.11.029

M3 - Article

AN - SCOPUS:85059313663

SN - 0032-3861

VL - 160

SP - 238

EP - 245

JO - polymer

JF - polymer

ER -

Investigation of hydrogen-bonding mediated molecular packing of diketopyrrolopyrrole based donor-acceptor oligomers in the solid state

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Keywords

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