2019
DOI: 10.1016/j.molstruc.2019.07.086
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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 palladiumcatalyzed Sonogashira coupling reactions. The structures of 1 and 2 were revealed through single-crystal X-ray analysis. Cyclotetramerization of these phthalonitriles led to the

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Cited by 10 publications
(7 citation statements)
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“…The first oxidation peak of 5 was 60 mV positively shifted in comparison with 4 as the result of the effect of the naphthalene ring. The HOMO level of 4 and 5 was calculated from the first oxidation, indicating the effective destabilization of the HOMO energy level which is caused by the introduction of different groups at the non-peripheral and peripheral positions of the Pc [20,26,28]. The optical band gap was calculated to be 1.58 and 1.56 eV for 4 and 5, respectively, which is slightly higher than the electrochemical band gap.…”
Section: Electrochemical Measurementsmentioning
confidence: 94%
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“…The first oxidation peak of 5 was 60 mV positively shifted in comparison with 4 as the result of the effect of the naphthalene ring. The HOMO level of 4 and 5 was calculated from the first oxidation, indicating the effective destabilization of the HOMO energy level which is caused by the introduction of different groups at the non-peripheral and peripheral positions of the Pc [20,26,28]. The optical band gap was calculated to be 1.58 and 1.56 eV for 4 and 5, respectively, which is slightly higher than the electrochemical band gap.…”
Section: Electrochemical Measurementsmentioning
confidence: 94%
“…In these studies, long alkyl chains, such as butoxy or hexyloxy, are attached to the non-peripheral positions of phthalocyanines to improve their solubility. Furthermore, if α-positions of Pcs were substituted with alkoxy substituents, a red-shifted Q band from 650 nm to 750 nm was observed, reducing the highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO-LUMO) gap [7,19,[22][23][24][25][26][27][28]. With respect to Kobayashi's papers from 2011 and 2014, non-peripherally S-, Se-, or Te-substituted Pcs exhibited Q bands beyond 1000 nm [29,30].…”
Section: Introductionmentioning
confidence: 90%
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“…[22][23][24][25][26][27][28] Due to the ease of the structural modification of Pcs, these macromolecules can be designed for special applications. [29][30][31][32] Additionally, axially substituted phthalocyanines bearing various ligand(s) on the metal center have attracted attention in recent years. [33][34][35][36] Among the axially substituted Pcs, silicon phthalocyanines (SiPcs) exhibit excellent biological properties owing to the unusual six-coordinated silicon (IV) ion and the possibility of symmetrically or unsymmetrically replacement of different axial ligands.…”
Section: Introductionmentioning
confidence: 99%
“…Also, some of the metal cations that have higher coordination numbers (more than 2) include axial ligands inserted into the ring center. [5][6][7][8][9][10][11][12][13][14][15] The presence of axial ligands in the structure of phthalocyanines intensively reduces the π-π interactions and results in much more soluble phthalocyanines. [1][2][3][4] Depending on a special function, different ligands can be placed in axial positions.…”
Section: Introductionmentioning
confidence: 99%