A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells

Pranabesh Dutta; Hanok Park; Woo Hyoung Lee; In Nam Kang; Soo Hyoung Lee

doi:10.1016/j.orgel.2012.09.019

A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells

Pranabesh Dutta
, Hanok Park
, Woo Hyoung Lee
, In Nam Kang
, Soo Hyoung Lee^*

^*Corresponding author for this work

Division of Chemical Engineering

Jeonbuk National University
The Catholic University of Korea

Research output: Contribution to journal › Journal article › peer-review

27 Scopus citations

Abstract

In this work, we have designed and synthesized a new naphtho[1,2-b:5,6- b′]dithiophene-containing enlarged π-conjugated donor-acceptor (D-A) small molecule, NDT(TTz)₂, for use in solution-processed organic photovoltaics. NDT(TTz)₂, which contains a thiophene-bridged naphtho[1,2-b:5,6-b′]dithiophene as the central fused core and triphenylamine-flanked thiophene thiazolothiazole as a spacer, was synthesized via sequential Suzuki and Stille coupling reactions. The thermal, physiochemical, and electrochemical properties of NDT(TTz)₂ have been evaluated by differential scanning calorimetry, thermogravimetry, UV-Vis spectroscopy, photoluminescence spectroscopy, X-ray diffraction, and cyclic voltammetry. As desired for photovoltaic applications, NDT(TTz)₂ possesses good solubility, thermal stability, and a well-ordered, π-π stacked, crystallinity. The optical band gap and HOMO level of NDT(TTz) ₂ were determined to be 2.0 eV and -5.23 eV, respectively. In addition to organic thin film transistor studies, application of NDT(TTz) ₂ to preliminary photovoltaic devices has also been investigated by fabricating solution-processed bulk heterojunction solar cells together with PC₇₁BM in a typical layered device structure, ITO/PEDOT:PSS/NDT(TTz) ₂:PC₇₁BM/LiF/Al. Without extensive optimization of the device, NDT(TTz)₂ in these devices shows a maximum power conversion efficiency of 1.44% under AM 1.5 illumination at a 100 mW/cm² intensity.

Original language	English
Pages (from-to)	3183-3194
Number of pages	12
Journal	Organic Electronics
Volume	13
Issue number	12
DOIs	https://doi.org/10.1016/j.orgel.2012.09.019
State	Published - 2012.12

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Keywords

Naphtho[12-b:5,6-b′]dithiophene
Organic solar cells
Power conversion efficiency
Small molecules
Solution-processable

Quacquarelli Symonds(QS) Subject Topics

Materials Science
Engineering - Electrical & Electronic
Engineering - Petroleum
Chemistry
Physics & Astronomy

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10.1016/j.orgel.2012.09.019

Cite this

@article{5a92f2baf45249158bf03be0408721df,

title = "A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells",

abstract = "In this work, we have designed and synthesized a new naphtho[1,2-b:5,6- b′]dithiophene-containing enlarged π-conjugated donor-acceptor (D-A) small molecule, NDT(TTz)2, for use in solution-processed organic photovoltaics. NDT(TTz)2, which contains a thiophene-bridged naphtho[1,2-b:5,6-b′]dithiophene as the central fused core and triphenylamine-flanked thiophene thiazolothiazole as a spacer, was synthesized via sequential Suzuki and Stille coupling reactions. The thermal, physiochemical, and electrochemical properties of NDT(TTz)2 have been evaluated by differential scanning calorimetry, thermogravimetry, UV-Vis spectroscopy, photoluminescence spectroscopy, X-ray diffraction, and cyclic voltammetry. As desired for photovoltaic applications, NDT(TTz)2 possesses good solubility, thermal stability, and a well-ordered, π-π stacked, crystallinity. The optical band gap and HOMO level of NDT(TTz) 2 were determined to be 2.0 eV and -5.23 eV, respectively. In addition to organic thin film transistor studies, application of NDT(TTz) 2 to preliminary photovoltaic devices has also been investigated by fabricating solution-processed bulk heterojunction solar cells together with PC71BM in a typical layered device structure, ITO/PEDOT:PSS/NDT(TTz) 2:PC71BM/LiF/Al. Without extensive optimization of the device, NDT(TTz)2 in these devices shows a maximum power conversion efficiency of 1.44\% under AM 1.5 illumination at a 100 mW/cm2 intensity.",

keywords = "Naphtho[12-b:5,6-b′]dithiophene, Organic solar cells, Power conversion efficiency, Small molecules, Solution-processable",

author = "Pranabesh Dutta and Hanok Park and Lee, \{Woo Hyoung\} and Kang, \{In Nam\} and Lee, \{Soo Hyoung\}",

year = "2012",

month = dec,

doi = "10.1016/j.orgel.2012.09.019",

language = "English",

volume = "13",

pages = "3183--3194",

journal = "Organic Electronics",

issn = "1566-1199",

number = "12",

}

TY - JOUR

T1 - A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells

AU - Dutta, Pranabesh

AU - Park, Hanok

AU - Lee, Woo Hyoung

AU - Kang, In Nam

AU - Lee, Soo Hyoung

PY - 2012/12

Y1 - 2012/12

N2 - In this work, we have designed and synthesized a new naphtho[1,2-b:5,6- b′]dithiophene-containing enlarged π-conjugated donor-acceptor (D-A) small molecule, NDT(TTz)2, for use in solution-processed organic photovoltaics. NDT(TTz)2, which contains a thiophene-bridged naphtho[1,2-b:5,6-b′]dithiophene as the central fused core and triphenylamine-flanked thiophene thiazolothiazole as a spacer, was synthesized via sequential Suzuki and Stille coupling reactions. The thermal, physiochemical, and electrochemical properties of NDT(TTz)2 have been evaluated by differential scanning calorimetry, thermogravimetry, UV-Vis spectroscopy, photoluminescence spectroscopy, X-ray diffraction, and cyclic voltammetry. As desired for photovoltaic applications, NDT(TTz)2 possesses good solubility, thermal stability, and a well-ordered, π-π stacked, crystallinity. The optical band gap and HOMO level of NDT(TTz) 2 were determined to be 2.0 eV and -5.23 eV, respectively. In addition to organic thin film transistor studies, application of NDT(TTz) 2 to preliminary photovoltaic devices has also been investigated by fabricating solution-processed bulk heterojunction solar cells together with PC71BM in a typical layered device structure, ITO/PEDOT:PSS/NDT(TTz) 2:PC71BM/LiF/Al. Without extensive optimization of the device, NDT(TTz)2 in these devices shows a maximum power conversion efficiency of 1.44% under AM 1.5 illumination at a 100 mW/cm2 intensity.

AB - In this work, we have designed and synthesized a new naphtho[1,2-b:5,6- b′]dithiophene-containing enlarged π-conjugated donor-acceptor (D-A) small molecule, NDT(TTz)2, for use in solution-processed organic photovoltaics. NDT(TTz)2, which contains a thiophene-bridged naphtho[1,2-b:5,6-b′]dithiophene as the central fused core and triphenylamine-flanked thiophene thiazolothiazole as a spacer, was synthesized via sequential Suzuki and Stille coupling reactions. The thermal, physiochemical, and electrochemical properties of NDT(TTz)2 have been evaluated by differential scanning calorimetry, thermogravimetry, UV-Vis spectroscopy, photoluminescence spectroscopy, X-ray diffraction, and cyclic voltammetry. As desired for photovoltaic applications, NDT(TTz)2 possesses good solubility, thermal stability, and a well-ordered, π-π stacked, crystallinity. The optical band gap and HOMO level of NDT(TTz) 2 were determined to be 2.0 eV and -5.23 eV, respectively. In addition to organic thin film transistor studies, application of NDT(TTz) 2 to preliminary photovoltaic devices has also been investigated by fabricating solution-processed bulk heterojunction solar cells together with PC71BM in a typical layered device structure, ITO/PEDOT:PSS/NDT(TTz) 2:PC71BM/LiF/Al. Without extensive optimization of the device, NDT(TTz)2 in these devices shows a maximum power conversion efficiency of 1.44% under AM 1.5 illumination at a 100 mW/cm2 intensity.

KW - Naphtho[12-b:5,6-b′]dithiophene

KW - Organic solar cells

KW - Power conversion efficiency

KW - Small molecules

KW - Solution-processable

UR - https://www.scopus.com/pages/publications/84867771388

U2 - 10.1016/j.orgel.2012.09.019

DO - 10.1016/j.orgel.2012.09.019

M3 - Journal article

AN - SCOPUS:84867771388

SN - 1566-1199

VL - 13

SP - 3183

EP - 3194

JO - Organic Electronics

JF - Organic Electronics

IS - 12

ER -

A crystalline D-π-A organic small molecule with naphtho[1,2-b:5,6- b′]dithiophene-core for solution processed organic solar cells

Abstract

UN SDGs

Keywords

Quacquarelli Symonds(QS) Subject Topics

Access to Document

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