Effect of alkyl chain topology on the structure, optoelectronic properties and solar cell performance of thienopyrroledione-cored oligothiophene chromophores

Bright Walker, Seungjib Yum, Bomee Jang, Jihyeon Kim, Taehyo Kim, Jin Young Kim, Han Young Woo

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

We have investigated a series of oligothiophenes containing a central thienopyrroledione group with rhodanine, dicyanovinyl and octylcyanoacrylate end-capping groups. For each end capping group, two alkyl chain configurations were explored by appending n-octyl chains to the oligothiophenes in both proximal and distal topologies. Substitution of different alkyl topologies and end-capping groups altered not only intramolecular conformations but also intermolecular interactions, thus affecting frontier molecular orbitals and bulk properties such as optical, thermal transitions, solid state packing, and device properties. The electronic properties of the materials were probed in field effect transistors (FETs), single carrier diodes and bulk heterojunction (BHJ) solar cell devices. FET devices revealed that all materials behaved as p-type semiconductors with mobilities in the range of 10-5 to 10-3 cm2 V-1 s-1. In solar cell devices, we observed that the optimal end capping group was rhodanine, while the optimal alkyl chain configuration was the proximal configuration. The rhodanine capped molecule with proximal alkyl chain isomerism led to a power conversion efficiency of ∼2%. Grazing-incidence wide-angle X-ray scattering studies of this series of molecules revealed a strong tendency to undergo edge-on packing with no π-π stacking in the vertical direction, which may limit their performance in BHJ solar cells.

Original languageEnglish
Pages (from-to)77655-77665
Number of pages11
JournalRSC Advances
Volume6
Issue number81
DOIs
Publication statusPublished - 2016 Jan 1

Fingerprint

Rhodanine
Chromophores
Optoelectronic devices
Solar cells
Topology
Field effect transistors
Heterojunctions
Molecules
Molecular orbitals
X ray scattering
Electronic properties
Conversion efficiency
Conformations
Diodes
Substitution reactions
Semiconductor materials

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Effect of alkyl chain topology on the structure, optoelectronic properties and solar cell performance of thienopyrroledione-cored oligothiophene chromophores. / Walker, Bright; Yum, Seungjib; Jang, Bomee; Kim, Jihyeon; Kim, Taehyo; Kim, Jin Young; Woo, Han Young.

In: RSC Advances, Vol. 6, No. 81, 01.01.2016, p. 77655-77665.

Research output: Contribution to journalArticle

Walker, Bright ; Yum, Seungjib ; Jang, Bomee ; Kim, Jihyeon ; Kim, Taehyo ; Kim, Jin Young ; Woo, Han Young. / Effect of alkyl chain topology on the structure, optoelectronic properties and solar cell performance of thienopyrroledione-cored oligothiophene chromophores. In: RSC Advances. 2016 ; Vol. 6, No. 81. pp. 77655-77665.
@article{394f3cab3c7a4630ab34fae8c489b889,
title = "Effect of alkyl chain topology on the structure, optoelectronic properties and solar cell performance of thienopyrroledione-cored oligothiophene chromophores",
abstract = "We have investigated a series of oligothiophenes containing a central thienopyrroledione group with rhodanine, dicyanovinyl and octylcyanoacrylate end-capping groups. For each end capping group, two alkyl chain configurations were explored by appending n-octyl chains to the oligothiophenes in both proximal and distal topologies. Substitution of different alkyl topologies and end-capping groups altered not only intramolecular conformations but also intermolecular interactions, thus affecting frontier molecular orbitals and bulk properties such as optical, thermal transitions, solid state packing, and device properties. The electronic properties of the materials were probed in field effect transistors (FETs), single carrier diodes and bulk heterojunction (BHJ) solar cell devices. FET devices revealed that all materials behaved as p-type semiconductors with mobilities in the range of 10-5 to 10-3 cm2 V-1 s-1. In solar cell devices, we observed that the optimal end capping group was rhodanine, while the optimal alkyl chain configuration was the proximal configuration. The rhodanine capped molecule with proximal alkyl chain isomerism led to a power conversion efficiency of ∼2{\%}. Grazing-incidence wide-angle X-ray scattering studies of this series of molecules revealed a strong tendency to undergo edge-on packing with no π-π stacking in the vertical direction, which may limit their performance in BHJ solar cells.",
author = "Bright Walker and Seungjib Yum and Bomee Jang and Jihyeon Kim and Taehyo Kim and Kim, {Jin Young} and Woo, {Han Young}",
year = "2016",
month = "1",
day = "1",
doi = "10.1039/c6ra17096j",
language = "English",
volume = "6",
pages = "77655--77665",
journal = "RSC Advances",
issn = "2046-2069",
publisher = "Royal Society of Chemistry",
number = "81",

}

TY - JOUR

T1 - Effect of alkyl chain topology on the structure, optoelectronic properties and solar cell performance of thienopyrroledione-cored oligothiophene chromophores

AU - Walker, Bright

AU - Yum, Seungjib

AU - Jang, Bomee

AU - Kim, Jihyeon

AU - Kim, Taehyo

AU - Kim, Jin Young

AU - Woo, Han Young

PY - 2016/1/1

Y1 - 2016/1/1

N2 - We have investigated a series of oligothiophenes containing a central thienopyrroledione group with rhodanine, dicyanovinyl and octylcyanoacrylate end-capping groups. For each end capping group, two alkyl chain configurations were explored by appending n-octyl chains to the oligothiophenes in both proximal and distal topologies. Substitution of different alkyl topologies and end-capping groups altered not only intramolecular conformations but also intermolecular interactions, thus affecting frontier molecular orbitals and bulk properties such as optical, thermal transitions, solid state packing, and device properties. The electronic properties of the materials were probed in field effect transistors (FETs), single carrier diodes and bulk heterojunction (BHJ) solar cell devices. FET devices revealed that all materials behaved as p-type semiconductors with mobilities in the range of 10-5 to 10-3 cm2 V-1 s-1. In solar cell devices, we observed that the optimal end capping group was rhodanine, while the optimal alkyl chain configuration was the proximal configuration. The rhodanine capped molecule with proximal alkyl chain isomerism led to a power conversion efficiency of ∼2%. Grazing-incidence wide-angle X-ray scattering studies of this series of molecules revealed a strong tendency to undergo edge-on packing with no π-π stacking in the vertical direction, which may limit their performance in BHJ solar cells.

AB - We have investigated a series of oligothiophenes containing a central thienopyrroledione group with rhodanine, dicyanovinyl and octylcyanoacrylate end-capping groups. For each end capping group, two alkyl chain configurations were explored by appending n-octyl chains to the oligothiophenes in both proximal and distal topologies. Substitution of different alkyl topologies and end-capping groups altered not only intramolecular conformations but also intermolecular interactions, thus affecting frontier molecular orbitals and bulk properties such as optical, thermal transitions, solid state packing, and device properties. The electronic properties of the materials were probed in field effect transistors (FETs), single carrier diodes and bulk heterojunction (BHJ) solar cell devices. FET devices revealed that all materials behaved as p-type semiconductors with mobilities in the range of 10-5 to 10-3 cm2 V-1 s-1. In solar cell devices, we observed that the optimal end capping group was rhodanine, while the optimal alkyl chain configuration was the proximal configuration. The rhodanine capped molecule with proximal alkyl chain isomerism led to a power conversion efficiency of ∼2%. Grazing-incidence wide-angle X-ray scattering studies of this series of molecules revealed a strong tendency to undergo edge-on packing with no π-π stacking in the vertical direction, which may limit their performance in BHJ solar cells.

UR - http://www.scopus.com/inward/record.url?scp=85018227151&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85018227151&partnerID=8YFLogxK

U2 - 10.1039/c6ra17096j

DO - 10.1039/c6ra17096j

M3 - Article

AN - SCOPUS:85018227151

VL - 6

SP - 77655

EP - 77665

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 81

ER -