Molecular Design Principles for Near-Infrared Absorbing and Emitting Indolizine Dyes

Aron J. Huckaba; Aswani Yella; Louis E. McNamara; April E. Steen; J. Scott Murphy; Casey A. Carpenter; George D. Puneky; Nathan I. Hammer; Mohammad Khaja Nazeeruddin; Michael Grätzel; Jared H. Delcamp

doi:10.1002/chem.201603165

Molecular Design Principles for Near-Infrared Absorbing and Emitting Indolizine Dyes

Aron J. Huckaba, Aswani Yella, Louis E. McNamara, April E. Steen, J. Scott Murphy, Casey A. Carpenter, George D. Puneky, Nathan I. Hammer, Mohammad Khaja Nazeeruddin, Michael Grätzel, Jared H. Delcamp

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

42 Scopus citations

Abstract

Desirable components for dye-sensitzed solar cell (DSC) sensitizers and fluorescent imaging dyes include strong donating building blocks coupled with well-balanced acceptor functionalities for absorption beyond the visible range. We have evaluated the effects of increasing acceptor strengths and incorporation of dye morphology controlling groups on molar absorptivity and absorption breadth with indolizine donor-based dyes. Indolizine-based D–A and D–π–A sensitizers incorporating bis-rhodanine, tricyanofuran (TCF), and cyanoacrylic acid functionalities were analyzed for performance in DSC devices. The TCF derivatives were also evaluated as near-infrared (NIR)-emissive materials with the AH25 emissions extending past 1000 nm.

Original language	English
Pages (from-to)	15536-15542
Number of pages	7
Journal	Chemistry - A European Journal
Volume	22
Issue number	43
DOIs	https://doi.org/10.1002/chem.201603165
State	Published - Oct 17 2016

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Funding

The authors A.J.H., J.S.M., G.D.P., C.A.C. and J.H.D. thank the Mississippi NSF-CAREER program (1455167), LEM and NIH thank the NSF OIA EPSCoR-Track 2 program (1539035), G.D.P. and J.S.M. thank the Sally McDonnell Barksdale Honors College, J.S.M. thanks the Ole Miss Physical Chemistry Summer Research Program NSF REU (CHE-1156713), and M.K.N., M.G., and A.Y. thank the European Community's Seventh Framework Programme (FP7/2007-2013) ENERGY.2012.10.2.1, NANOMATCELL, Grant agreement no: 308997.

Funders	Funder number
Sally McDonnell Barksdale Honors College	CHE-1156713
National Science Foundation (NSF)	1539035, 1156713
Seventh Framework Programme	308997
Seventh Framework Programme

Keywords

NIR dye
donor–acceptor systems
dye-sensitized solar cells
dyes/pigments
indolizine

ASJC Scopus subject areas

General Chemistry
Catalysis
Organic Chemistry

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10.1002/chem.201603165

Cite this

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title = "Molecular Design Principles for Near-Infrared Absorbing and Emitting Indolizine Dyes",

abstract = "Desirable components for dye-sensitzed solar cell (DSC) sensitizers and fluorescent imaging dyes include strong donating building blocks coupled with well-balanced acceptor functionalities for absorption beyond the visible range. We have evaluated the effects of increasing acceptor strengths and incorporation of dye morphology controlling groups on molar absorptivity and absorption breadth with indolizine donor-based dyes. Indolizine-based D–A and D–π–A sensitizers incorporating bis-rhodanine, tricyanofuran (TCF), and cyanoacrylic acid functionalities were analyzed for performance in DSC devices. The TCF derivatives were also evaluated as near-infrared (NIR)-emissive materials with the AH25 emissions extending past 1000 nm.",

keywords = "NIR dye, donor–acceptor systems, dye-sensitized solar cells, dyes/pigments, indolizine",

author = "Huckaba, {Aron J.} and Aswani Yella and McNamara, {Louis E.} and Steen, {April E.} and Murphy, {J. Scott} and Carpenter, {Casey A.} and Puneky, {George D.} and Hammer, {Nathan I.} and Nazeeruddin, {Mohammad Khaja} and Michael Gr{\"a}tzel and Delcamp, {Jared H.}",

note = "Publisher Copyright: {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2016",

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doi = "10.1002/chem.201603165",

language = "English",

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AU - Huckaba, Aron J.

AU - Yella, Aswani

AU - McNamara, Louis E.

AU - Steen, April E.

AU - Murphy, J. Scott

AU - Carpenter, Casey A.

AU - Puneky, George D.

AU - Hammer, Nathan I.

AU - Nazeeruddin, Mohammad Khaja

AU - Grätzel, Michael

AU - Delcamp, Jared H.

PY - 2016/10/17

Y1 - 2016/10/17

N2 - Desirable components for dye-sensitzed solar cell (DSC) sensitizers and fluorescent imaging dyes include strong donating building blocks coupled with well-balanced acceptor functionalities for absorption beyond the visible range. We have evaluated the effects of increasing acceptor strengths and incorporation of dye morphology controlling groups on molar absorptivity and absorption breadth with indolizine donor-based dyes. Indolizine-based D–A and D–π–A sensitizers incorporating bis-rhodanine, tricyanofuran (TCF), and cyanoacrylic acid functionalities were analyzed for performance in DSC devices. The TCF derivatives were also evaluated as near-infrared (NIR)-emissive materials with the AH25 emissions extending past 1000 nm.

AB - Desirable components for dye-sensitzed solar cell (DSC) sensitizers and fluorescent imaging dyes include strong donating building blocks coupled with well-balanced acceptor functionalities for absorption beyond the visible range. We have evaluated the effects of increasing acceptor strengths and incorporation of dye morphology controlling groups on molar absorptivity and absorption breadth with indolizine donor-based dyes. Indolizine-based D–A and D–π–A sensitizers incorporating bis-rhodanine, tricyanofuran (TCF), and cyanoacrylic acid functionalities were analyzed for performance in DSC devices. The TCF derivatives were also evaluated as near-infrared (NIR)-emissive materials with the AH25 emissions extending past 1000 nm.

KW - NIR dye

KW - donor–acceptor systems

KW - dye-sensitized solar cells

KW - dyes/pigments

KW - indolizine

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JF - Chemistry - A European Journal

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ER -

Molecular Design Principles for Near-Infrared Absorbing and Emitting Indolizine Dyes

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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