Near-infrared absorbing π-extended hexadeca substituted phthalocyanines

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

*Kontaktforfatter for dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

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.

OriginalsprogEngelsk
TidsskriftJournal of Molecular Structure
Vol/bind1197
Sider (fra-til)736-741
Antal sider6
ISSN0022-2860
DOI
StatusUdgivet - 5. dec. 2019

Fingeraftryk

destabilization
conjugation
palladium
energy levels
substitutes
Infrared radiation
oxidation
shift
single crystals
X ray analysis
Palladium
wavelengths
Electron energy levels
x rays
Substitution reactions
X-Rays
Single crystals
Wavelength
Oxidation
diphenyl

Citer dette

Karaoğlu, H. P., Atsay, A., Nar, I., McKee, V., Koçak, M. B., Hamuryudan, E., & Gül, A. (2019). Near-infrared absorbing π-extended hexadeca substituted phthalocyanines. Journal of Molecular Structure, 1197, 736-741. https://doi.org/10.1016/j.molstruc.2019.07.086
Karaoğlu, Hande Pekbelgin ; Atsay, Armağan ; Nar, Ilgın ; McKee, Vickie ; Koçak, Makbule B. ; Hamuryudan, Esin ; Gül, Ahmet. / Near-infrared absorbing π-extended hexadeca substituted phthalocyanines. I: Journal of Molecular Structure. 2019 ; Bind 1197. s. 736-741.
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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{\cc}ak, {Makbule B.} and Esin Hamuryudan and Ahmet G{\"u}l",
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Near-infrared absorbing π-extended hexadeca substituted phthalocyanines. / Karaoğlu, Hande Pekbelgin; Atsay, Armağan; Nar, Ilgın; McKee, Vickie; Koçak, Makbule B.; Hamuryudan, Esin; Gül, Ahmet.

I: Journal of Molecular Structure, Bind 1197, 05.12.2019, s. 736-741.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

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

U2 - 10.1016/j.molstruc.2019.07.086

DO - 10.1016/j.molstruc.2019.07.086

M3 - Journal article

VL - 1197

SP - 736

EP - 741

JO - Computational and Theoretical Chemistry

JF - Computational and Theoretical Chemistry

SN - 2210-271X

ER -