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 |
|---|---|
| Journal | Journal of Molecular Structure |
| Volume | 1197 |
| Pages (from-to) | 736-741 |
| Number of pages | 6 |
| ISSN | 0022-2860 |
| DOIs | |
| Publication status | Published - 5. Dec 2019 |
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Keywords
- Biphenylethynyl
- Diphenylacetylenethynyl
- Extended pi conjugation
- Near IR absorption
- Phthalocyanine
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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.
In: Journal of Molecular Structure, Vol. 1197, 05.12.2019, p. 736-741.Research output: Contribution to journal › Journal article › Research › peer-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 -