2004
DOI: 10.1002/chem.200400275
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Synthesis, Spectroscopy, and Electrochemistry of Tetra‐tert‐butylated Tetraazaporphyrins, Phthalocyanines, Naphthalocyanines, and Anthracocyanines, together with Molecular Orbital Calculations

Abstract: Tetraazaporphyrins (TAPs), phthalocyanines (Pcs), naphthalocyanines (Ncs), and anthracocyanines (Acs) with four tert-butyl groups attached at similar positions have been synthesized, and their electronic absorption, magnetic circular dichroism (MCD), IR, and voltammetric properties were studied and interpreted with the help of quantum-mechanical calculations. Through the preparation of a series of compounds with the same number of the same substituent, the effects of the increase in the size of the ring system… Show more

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Cited by 173 publications
(165 citation statements)
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“…But the wellknown NIR photosensitizer zinc naphthalocyanine Zn4 is significantly less stable. The decreased photostability of naphthalocyanines [31,32] and antracenocyanines is well-known and can be explained by the destabilization of HOMO which was estimated from calculations [31] and electrochemistry [14,32]). In contrast, upon annelation of two or more Pc units via a shared benzene ring, the HOMO-LUMO gap (responsible for E exc ) is reduced to a greater extent by LUMO stabilization [33,34] than by HOMO destabilization (see Fig.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…But the wellknown NIR photosensitizer zinc naphthalocyanine Zn4 is significantly less stable. The decreased photostability of naphthalocyanines [31,32] and antracenocyanines is well-known and can be explained by the destabilization of HOMO which was estimated from calculations [31] and electrochemistry [14,32]). In contrast, upon annelation of two or more Pc units via a shared benzene ring, the HOMO-LUMO gap (responsible for E exc ) is reduced to a greater extent by LUMO stabilization [33,34] than by HOMO destabilization (see Fig.…”
Section: Resultsmentioning
confidence: 99%
“…One type of NIR-absorbing phthalocyanine analogs are well-known naphthalocyanines (Nc) [13,14] and anthracenocyanines (Ac) [14,15]. However, their stability is significantly reduced compared to Pcs.…”
Section: Introductionmentioning
confidence: 99%
“…Metal-free 4 exhibits Q-band splitting ( Figure 1a), that can be attributed to the non-degenerated LUMO orbital. [14] In contrast, Q-bands in complexes 2, 3, 5 were not split ( Figure 1 and Table 1). This result is in accord with the literature data [15] and DFT calculations [14] for porphyrazines.…”
Section: Treatment Of Magnesium Complexmentioning
confidence: 95%
“…[14] In contrast, Q-bands in complexes 2, 3, 5 were not split ( Figure 1 and Table 1). This result is in accord with the literature data [15] and DFT calculations [14] for porphyrazines. The absence of Q-band splitting and the values of full width at half maximum (FWHM) for porphyrazine complexes in THF (Table 1.)…”
Section: Treatment Of Magnesium Complexmentioning
confidence: 95%
“…[1][2][3][4] It is known that the widening of the conjugation system causes a considerable (up to 100 nm) bathochromic shift of the Q-band in the electronic absorption spectra of naphthalocyanines in comparison with the spectra of phthalocyanines. [5][6][7][8] An introduction of functional groups into naphthalocyanine ligands, a possibility of a central ion incorporation into the macrocycle, and an ability, similarly to phthalocyanines, to form double decker complexes allows one to vary their properties within a wide range.…”
Section: Introductionmentioning
confidence: 99%