Functional Organic Semiconductors Based on Bay-Annulated Indigo (BAI)

Kolaczkowski, Matthew A.; Liu, Yi

doi:10.1002/tcr.201800159

Title: Functional Organic Semiconductors Based on Bay-Annulated Indigo (BAI)

Journal Article · 21 January 2019 · Chemical Record

DOI: https://doi.org/10.1002/tcr.201800159 · OSTI ID:1506402

Kolaczkowski, Matthew A. ^[1];

^[2]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Here, we report the advancement of organic electronics has been continually pushed by the need for stable and high performance acceptor materials. By utilizing inexpensive and stable indigo dye as a starting material, Bay-Annulated Indigo (BAI) provides a new motif for the development of semiconducting materials. Modular and straightforward synthesis makes BAI an outstanding platform for molecular design, while excellent stability, strong absorption, and high ambipolar mobility render BAI-based materials excellent candidates for organic electronics. BAI-based polymers and small molecules have taken advantage of these properties to show promising results in a variety of applications.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1506402

Journal Information:: Chemical Record, Journal Name: Chemical Record Vol. 19; ISSN 1527-8999

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (51)

Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N-Type Mobility Indolonaphthyridine Polymers Fallon, Kealan J.; Santala, Annikki; Wijeyasinghe, Nilushi Advanced Functional Materials, Vol. 27, Issue 43 https://doi.org/10.1002/adfm.201704069	journal	September 2017
Indigo - A Natural Pigment for High Performance Ambipolar Organic Field Effect Transistors and Circuits Irimia-Vladu, Mihai; Głowacki, Eric D.; Troshin, Pavel A. Advanced Materials, Vol. 24, Issue 3 https://doi.org/10.1002/adma.201102619	journal	November 2011
25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors Zhao, Yan; Guo, Yunlong; Liu, Yunqi Advanced Materials, Vol. 25, Issue 38 https://doi.org/10.1002/adma.201302315	journal	August 2013
An Electron Acceptor Challenging Fullerenes for Efficient Polymer Solar Cells Lin, Yuze; Wang, Jiayu; Zhang, Zhi-Guo Advanced Materials, Vol. 27, Issue 7 https://doi.org/10.1002/adma.201404317	journal	January 2015
Diketopyrrolopyrrole-Based Semiconducting Polymer Nanoparticles for In Vivo Photoacoustic Imaging Pu, Kanyi; Mei, Jianguo; Jokerst, Jesse V. Advanced Materials, Vol. 27, Issue 35 https://doi.org/10.1002/adma.201502285	journal	August 2015
On the Study of Exciton Binding Energy with Direct Charge Generation in Photovoltaic Polymers Li, Ho-Wa; Guan, Zhiqiang; Cheng, Yuanhang Advanced Electronic Materials, Vol. 2, Issue 11 https://doi.org/10.1002/aelm.201600200	journal	September 2016
Über neue Derivate des Indigos und anderer indigoider Farbstoffe Engi, G. Zeitschrift für Angewandte Chemie, Vol. 27, Issue 20 https://doi.org/10.1002/ange.19140272003	journal	March 1914
Darstellung von Indigblau aus Orthonitrobenzaldehyd Baeyer, Adolf; Drewsen, Viggo Berichte der deutschen chemischen Gesellschaft, Vol. 15, Issue 2 https://doi.org/10.1002/cber.188201502274	journal	July 1882
Beiträge zur Kenntnis der Indigo-Gruppe, V.: Über einige Abkömmlinge des Thioindigos Posner, Theodor; Wallis, Ernst Berichte der deutschen chemischen Gesellschaft (A and B Series), Vol. 57, Issue 9 https://doi.org/10.1002/cber.19240570909	journal	October 1924
Bay Annulated Indigo as a New Chromophore for p-type Dye-Sensitized Solar Cells Summers, Gareth H.; Gibson, Elizabeth A. ChemPhotoChem, Vol. 2, Issue 6 https://doi.org/10.1002/cptc.201700153	journal	April 2018
Bay-annulated indigo based near-infrared sensitive polymer for organic solar cells Zhu, Jingshuai; Li, Tengfei; Shi, Keli Journal of Polymer Science Part A: Polymer Chemistry, Vol. 56, Issue 2 https://doi.org/10.1002/pola.28887	journal	November 2017
Enhancing the Efficiency of Organic Photovoltaics by a Photoactive Molecular Mediator Yang, Bin; Kolaczkowski, Matthew A.; Brady, Michael A. Solar RRL, Vol. 2, Issue 1 https://doi.org/10.1002/solr.201700208	journal	December 2017
Exciton binding energies in organic semiconductors Knupfer, M. Applied Physics A, Vol. 77, Issue 5 https://doi.org/10.1007/s00339-003-2182-9	journal	October 2003
Bay-annulated indigo derivatives based on a core of spiro[fluorene-9,9′-xanthene]: Synthesis, photophysical, and electrochemical properties Ren, Bao-Yi; Xu, Qin; Kolaczkowski, Matthew Dyes and Pigments, Vol. 160 https://doi.org/10.1016/j.dyepig.2018.07.042	journal	January 2019
Low bandgap polymers based on bay-annulated indigo for organic photovoltaics: Enhanced sustainability in material design and solar cell fabrication Brebels, Jeroen; Klider, Karine C. C. W. S.; Kelchtermans, Mathias Organic Electronics, Vol. 50 https://doi.org/10.1016/j.orgel.2017.07.037	journal	November 2017
Synthesis and peripheral substituent effects of bay-annulated indigo derivatives Furuyama, Taniyuki; Tamura, Daichi; Maeda, Hajime Tetrahedron Letters, Vol. 59, Issue 30 https://doi.org/10.1016/j.tetlet.2018.06.036	journal	July 2018
Oligomer Molecules for Efficient Organic Photovoltaics Lin, Yuze; Zhan, Xiaowei Accounts of Chemical Research, Vol. 49, Issue 2 https://doi.org/10.1021/acs.accounts.5b00363	journal	November 2015
The Curious Case of Fluorination of Conjugated Polymers for Solar Cells Zhang, Qianqian; Kelly, Mary Allison; Bauer, Nicole Accounts of Chemical Research, Vol. 50, Issue 9 https://doi.org/10.1021/acs.accounts.7b00326	journal	August 2017
Tunable Semiconducting Polymer Nanoparticles with INDT-Based Conjugated Polymers for Photoacoustic Molecular Imaging Stahl, Thomas; Bofinger, Robin; Lam, Ivan Bioconjugate Chemistry, Vol. 28, Issue 6 https://doi.org/10.1021/acs.bioconjchem.7b00185	journal	May 2017
Indolo-naphthyridine-6,13-dione Thiophene Building Block for Conjugated Polymer Electronics: Molecular Origin of Ultrahigh n-Type Mobility Fallon, Kealan J.; Wijeyasinghe, Nilushi; Manley, Eric F. Chemistry of Materials, Vol. 28, Issue 22 https://doi.org/10.1021/acs.chemmater.6b03671	journal	November 2016
A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells Fallon, Kealan J.; Wijeyasinghe, Nilushi; Yaacobi-Gross, Nir Macromolecules, Vol. 48, Issue 15 https://doi.org/10.1021/acs.macromol.5b00542	journal	July 2015
Sequential Fluorination on Napthaleneamide-Based Conjugated Polymers and Their Impact on Charge Transport Properties Kranthiraja, Kakaraparthi; Long, Dang Xuan; Sree, Vijaya Gopalan Macromolecules, Vol. 51, Issue 15 https://doi.org/10.1021/acs.macromol.8b00748	journal	July 2018
Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs Kolaczkowski, Matthew A.; He, Bo; Liu, Yi Organic Letters, Vol. 18, Issue 20 https://doi.org/10.1021/acs.orglett.6b02504	journal	October 2016
Low Bandgap Conjugated Polymers Based on a Nature-Inspired Bay-Annulated Indigo (BAI) Acceptor as Stable Electrochromic Materials He, Bo; Neo, Wei Teng; Chen, Teresa L. ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 5 https://doi.org/10.1021/acssuschemeng.6b00303	journal	April 2016
Alkyl Chain Length Dependence of the Field-Effect Mobility in Novel Anthracene Derivatives Back, Jang Yeol; An, Tae Kyu; Cheon, Ye Rim ACS Applied Materials & Interfaces, Vol. 7, Issue 1 https://doi.org/10.1021/am5063103	journal	December 2014
Recent Progress in Organic Electronics: Materials, Devices, and Processes Kelley, Tommie W.; Baude, Paul F.; Gerlach, Chris Chemistry of Materials, Vol. 16, Issue 23 https://doi.org/10.1021/cm049614j	journal	November 2004
π-Building Blocks for Organic Electronics: Revaluation of “Inductive” and “Resonance” Effects of π-Electron Deficient Units Takimiya, Kazuo; Osaka, Itaru; Nakano, Masahiro Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm4021063	journal	September 2013
Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications Beaujuge, Pierre M.; Fréchet, Jean M. J. Journal of the American Chemical Society, Vol. 133, Issue 50, p. 20009-20029 https://doi.org/10.1021/ja2073643	journal	December 2011
Systematic Investigation of Benzodithiophene- and Diketopyrrolopyrrole-Based Low-Bandgap Polymers Designed for Single Junction and Tandem Polymer Solar Cells Dou, Letian; Gao, Jing; Richard, Eric Journal of the American Chemical Society, Vol. 134, Issue 24 https://doi.org/10.1021/ja301460s	journal	June 2012
New Form of an Old Natural Dye: Bay-Annulated Indigo (BAI) as an Excellent Electron Accepting Unit for High Performance Organic Semiconductors He, Bo; Pun, Andrew B.; Zherebetskyy, Danylo Journal of the American Chemical Society, Vol. 136, Issue 42 https://doi.org/10.1021/ja508807m	journal	October 2014
Poly(diketopyrrolopyrrole−terthiophene) for Ambipolar Logic and Photovoltaics Bijleveld, Johan C.; Zoombelt, Arjan P.; Mathijssen, Simon G. J. Journal of the American Chemical Society, Vol. 131, Issue 46 https://doi.org/10.1021/ja907506r	journal	November 2009
Photophysics of an Indigo Derivative (Keto and Leuco Structures) with Singular Properties Seixas de Melo, J.; Rondão, R.; Burrows, H. D. The Journal of Physical Chemistry A, Vol. 110, Issue 51 https://doi.org/10.1021/jp057451w	journal	December 2006
Benzodipyrrolidones and Their Polymers Cui, Weibin; Yuen, Jonathan; Wudl, Fred Macromolecules, Vol. 44, Issue 20 https://doi.org/10.1021/ma2017293	journal	October 2011
Made to order Mann, John Nature, Vol. 341, Issue 6238 https://doi.org/10.1038/341118a0	journal	September 1989
Non-fullerene acceptors for organic solar cells Yan, Cenqi; Barlow, Stephen; Wang, Zhaohui Nature Reviews Materials, Vol. 3, Issue 3 https://doi.org/10.1038/natrevmats.2018.3	journal	February 2018
Made to order Facchetti, Antonio Nature Materials, Vol. 12, Issue 7 https://doi.org/10.1038/nmat3686	journal	June 2013
Next-generation organic photovoltaics based on non-fullerene acceptors Cheng, Pei; Li, Gang; Zhan, Xiaowei Nature Photonics, Vol. 12, Issue 3 https://doi.org/10.1038/s41566-018-0104-9	journal	February 2018
Molecular mechanisms of the photostability of indigo Yamazaki, Shohei; Sobolewski, Andrzej L.; Domcke, Wolfgang Phys. Chem. Chem. Phys., Vol. 13, Issue 4 https://doi.org/10.1039/C0CP01901A	journal	January 2011
The structural evolution of an isoindigo-based non-fullerene acceptor for use in organic photovoltaics McAfee, Seth M.; Topple, Jessica M.; Sun, Jon-Paul RSC Advances, Vol. 5, Issue 97 https://doi.org/10.1039/C5RA16696A	journal	January 2015
An indigo-based polymer bearing thermocleavable side chains for n-type organic thin film transistors Guo, Chang; Quinn, Jesse; Sun, Bin Journal of Materials Chemistry C, Vol. 3, Issue 20 https://doi.org/10.1039/C5TC00512D	journal	January 2015
Rational tuning of high-energy visible light absorption for panchromatic small molecules by a two-dimensional conjugation approach He, Bo; Zherebetskyy, Danylo; Wang, Hongxia Chemical Science, Vol. 7, Issue 6 https://doi.org/10.1039/C6SC00428H	journal	January 2016
Recent progress in non-fullerene small molecule acceptors in organic solar cells (OSCs) Chen, Wangqiao; Zhang, Qichun Journal of Materials Chemistry C, Vol. 5, Issue 6 https://doi.org/10.1039/C6TC05066B	journal	January 2017
Structures and properties of conjugated Donor–Acceptor copolymers for solar cell applications Zhang, Zhi–Guo; Wang, Jizheng Journal of Materials Chemistry, Vol. 22, Issue 10 https://doi.org/10.1039/c2jm14951f	journal	January 2012
UV∕ozone treated Au for air-stable, low hole injection barrier electrodes in organic electronics Rentenberger, S.; Vollmer, A.; Zojer, E. Journal of Applied Physics, Vol. 100, Issue 5 https://doi.org/10.1063/1.2336345	journal	September 2006
Made to Order: Japan Poulton, Cody Performance Research, Vol. 23, Issue 4-5 https://doi.org/10.1080/13528165.2018.1506416	journal	July 2018
Made to order Gaunt, Catherine Nursery World, Vol. 2015, Issue Sup23 https://doi.org/10.12968/nuwa.2015.sup23.14	journal	November 2015
The Curious Case of Fluorination of Conjugated Polymers for Solar Cells Q., Zhang,; W., You,; N., Bauer, The University of North Carolina at Chapel Hill University Libraries https://doi.org/10.17615/z62m-4b22	text	January 2017
Tunable Semiconducting Polymer Nanoparticles with INDT-Based Conjugated Polymers for Photoacoustic Molecular Imaging. Stahl, Thomas; Bofinger, Robin; Lam, Ivan Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.20271	text	January 2017
Effect of Alkyl Chain Branching Point on 3D Crystallinity in High N-Type Mobility Indolonaphthyridine Polymers Fallon, Kj; Santala, A.; Wijeyasinghe, N. Wiley-Blackwell https://doi.org/10.17863/cam.20274	journalarticle	January 2017
Indolo-naphthyridine-6,13-dione thiophene building block for conjugated polymer electronics: Molecular origin of ultrahigh n-type mobility Fallon, Kj; Wijeyasinghe, N.; Manley, Ef American Chemical Society (ACS) https://doi.org/10.17863/cam.20275	journalarticle	January 2016
A Nature-Inspired Conjugated Polymer for High Performance Transistors and Solar Cells Fallon, Kealan; Wijeyasinghe, N.; Yaacobi-Gross, N. Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.20285	text	January 2015

Cited By (1)

Synthesis and Properties of a Bay-Annulated-Indigo Tetramer Based on Low-Cost Spiro[Fluorene-9,9′-Xanthene] Core Ren, Bao-Yi; Tan, Yan-Mei; Sun, Chang-Liang Molecules, Vol. 24, Issue 19 https://doi.org/10.3390/molecules24193623	journal	October 2019

Similar Records

Bay-annulated indigo (BAI) as an excellent electron accepting building block for high performance organic semiconductors

Patent · 2015 · OSTI ID:1226805

Liu, Yi; He, Bo; Pun, Andrew

Bay-annulated indigo (BAI) as an excellent electron accepting building block for high performance organic semiconductors

Patent · 2016 · OSTI ID:1248011

Liu, Yi; He, Bo; Pun, Andrew

Stepwise Bay Annulation of Indigo for the Synthesis of Desymmetrized Electron Acceptors and Donor–Acceptor Constructs

Journal Article · 2016 · Organic Letters · OSTI ID:1437951

Kolaczkowski, Matthew A.; He, Bo; Liu, Yi

Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Bay-Annulated Indigo
Electron Acceptor
Indigo Organic Photovoltaics Panchromatic Absorption

Title: Functional Organic Semiconductors Based on Bay-Annulated Indigo (BAI)

Citation Formats

References (51)

Cited By (1)

Similar Records

Related Subjects