Near-infrared absorbing π-extended hexadeca substituted phthalocyanines

Hande Pekbelgin Karaoğlu; Armağan Atsay; Ilgın Nar; Vickie McKee; Makbule B. Koçak; Esin Hamuryudan; Ahmet Gül

doi:10.1016/j.molstruc.2019.07.086

Near-infrared absorbing π-extended hexadeca substituted phthalocyanines

Hande Pekbelgin Karaoğlu^*, Armağan Atsay, Ilgın Nar, Vickie McKee, Makbule B. Koçak, Esin Hamuryudan, Ahmet Gül

^*Corresponding author for this work

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

10 Citations (Scopus)

Abstract

Two new phthalonitriles 1 and 2, extended with biphenylethynyl and diphenylacetylenyl, were synthesized through a combination of Corey-Fuchs and palladium-catalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the corresponding 1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octakis(biphenyl) and (diphenylacetylenyl) phthalocyanines. The longer substituent, namely diphenylacetylenyl, is slightly more effective than biphenyl in shifting the Q band to a longer wavelength. A cathodic shift in first oxidation potential indicated the destabilization of the HOMO energy levels that results from non-peripheral substitution and extended π-conjugation.

Original language	English
Pages (from-to)	736-741
Number of pages	6
Journal	Journal of Molecular Structure
Volume	1197
DOIs	https://doi.org/10.1016/j.molstruc.2019.07.086
Publication status	Published - 5 Dec 2019

Bibliographical note

Publisher Copyright:
© 2019 Elsevier B.V.

Funding

This study was supported by the Research Fund of Istanbul Technical University . AG thanks Turkish Academy of Sciences (TUBA) for partial support. This study was supported by the Research Fund of Istanbul Technical University. AG thanks Turkish Academy of Sciences (TUBA) for partial support.

Funders	Funder number
TUBA
TÃ¼rkiye Bilimler Akademisi
Istanbul Teknik Üniversitesi

Keywords

Biphenylethynyl
Diphenylacetylenethynyl
Extended pi conjugation
Near IR absorption
Phthalocyanine

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10.1016/j.molstruc.2019.07.086

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title = "Near-infrared absorbing π-extended hexadeca substituted phthalocyanines",

abstract = "Two new phthalonitriles 1 and 2, extended with biphenylethynyl and diphenylacetylenyl, were synthesized through a combination of Corey-Fuchs and palladium-catalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the corresponding 1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octakis(biphenyl) and (diphenylacetylenyl) phthalocyanines. The longer substituent, namely diphenylacetylenyl, is slightly more effective than biphenyl in shifting the Q band to a longer wavelength. A cathodic shift in first oxidation potential indicated the destabilization of the HOMO energy levels that results from non-peripheral substitution and extended π-conjugation.",

keywords = "Biphenylethynyl, Diphenylacetylenethynyl, Extended pi conjugation, Near IR absorption, Phthalocyanine",

author = "Karaoğlu, {Hande Pekbelgin} and Armağan Atsay and Ilgın Nar and Vickie McKee and Ko{\c c}ak, {Makbule B.} and Esin Hamuryudan and Ahmet G{\"u}l",

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year = "2019",

month = dec,

day = "5",

doi = "10.1016/j.molstruc.2019.07.086",

language = "English",

volume = "1197",

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T1 - Near-infrared absorbing π-extended hexadeca substituted phthalocyanines

AU - Karaoğlu, Hande Pekbelgin

AU - Atsay, Armağan

AU - Nar, Ilgın

AU - McKee, Vickie

AU - Koçak, Makbule B.

AU - Hamuryudan, Esin

AU - Gül, Ahmet

PY - 2019/12/5

Y1 - 2019/12/5

N2 - Two new phthalonitriles 1 and 2, extended with biphenylethynyl and diphenylacetylenyl, were synthesized through a combination of Corey-Fuchs and palladium-catalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the corresponding 1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octakis(biphenyl) and (diphenylacetylenyl) phthalocyanines. The longer substituent, namely diphenylacetylenyl, is slightly more effective than biphenyl in shifting the Q band to a longer wavelength. A cathodic shift in first oxidation potential indicated the destabilization of the HOMO energy levels that results from non-peripheral substitution and extended π-conjugation.

AB - Two new phthalonitriles 1 and 2, extended with biphenylethynyl and diphenylacetylenyl, were synthesized through a combination of Corey-Fuchs and palladium-catalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the corresponding 1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octakis(biphenyl) and (diphenylacetylenyl) phthalocyanines. The longer substituent, namely diphenylacetylenyl, is slightly more effective than biphenyl in shifting the Q band to a longer wavelength. A cathodic shift in first oxidation potential indicated the destabilization of the HOMO energy levels that results from non-peripheral substitution and extended π-conjugation.

KW - Biphenylethynyl

KW - Diphenylacetylenethynyl

KW - Extended pi conjugation

KW - Near IR absorption

KW - Phthalocyanine

UR - http://www.scopus.com/inward/record.url?scp=85070020643&partnerID=8YFLogxK

U2 - 10.1016/j.molstruc.2019.07.086

DO - 10.1016/j.molstruc.2019.07.086

M3 - Article

AN - SCOPUS:85070020643

SN - 0022-2860

VL - 1197

SP - 736

EP - 741

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

ER -

Near-infrared absorbing π-extended hexadeca substituted phthalocyanines

Abstract

Bibliographical note

Funding

Keywords

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