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

Department of Chemistry

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.

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",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = dec,

day = "5",

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

language = "English",

volume = "1197",

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TY - JOUR

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

Keywords

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