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2008
DOI: 10.1021/ol8008842
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Synthesis and Characterization of Tetraanthroporphyrins

Abstract: Linearly pi-expanded novel tetraanthroporphyrins with and without aromatic rings at the meso-positions were prepared quantitatively for the first time from the corresponding precursors by a retro-Diels-Alder reaction.

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Cited by 68 publications
(25 citation statements)
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“…The trends in the MO energies of the frontier π -MOs and in the HOMO-LUMO gaps of the analogous set of fused-ring-expanded phthalonitriles (39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54), shown in Figure 7, are also broadly similar to those predicted for the corresponding Pc (1-22) and aza-BODIPY (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38) analogues. The alignments of the nodal planes of the a and s MOs (Figure 8) are similar to those of the corresponding tetraazapophyrin analogues (Figure 3), as would be anticipated based on their radial symmetry and the manner in which the 4 angular nodal planes lie on alternating sets of 8 atoms on the inner perimeter due to the M L = ± 4 properties.…”
Section: Resultssupporting
confidence: 69%
“…The trends in the MO energies of the frontier π -MOs and in the HOMO-LUMO gaps of the analogous set of fused-ring-expanded phthalonitriles (39)(40)(41)(42)(43)(44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54), shown in Figure 7, are also broadly similar to those predicted for the corresponding Pc (1-22) and aza-BODIPY (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38) analogues. The alignments of the nodal planes of the a and s MOs (Figure 8) are similar to those of the corresponding tetraazapophyrin analogues (Figure 3), as would be anticipated based on their radial symmetry and the manner in which the 4 angular nodal planes lie on alternating sets of 8 atoms on the inner perimeter due to the M L = ± 4 properties.…”
Section: Resultssupporting
confidence: 69%
“…This renders them very interesting candidates for the fabrication of solar cells. Surprisingly, up to now there has been only one publication dealing with the possible incorporation of porphycenes into solar cells 17…”
Section: Methodsmentioning
confidence: 99%
“…Up to date only one representative of TAPs has been shown to act as a sensitizer for TTA-UC. 19 These researchers noticed poor solubility, heavy aggregation and low stability towards oxidation of the obtained materials. Generally, TAPs have long remained elusive compounds.…”
Section: Introductionmentioning
confidence: 99%