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Real Optical Absorption Spectra Observed in Laboratories

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Optical Spectra of Phthalocyanines and Related Compounds

Part of the book series: NIMS Monographs ((NIMSM))

Abstract

In this chapter, some factors that internally and externally affect the optical absorption spectra of phthalocyanine derivatives and related macrocyclic compounds are described and it is illustrated how they contribute to the deviation from the prototypical spectrum. The internal factors include the type and position of substituent(s) on the periphery of the macrocycle, the expansion of the π-conjugation system, the nature of the metal ion in the cavity of the macrocycle (ion size, oxidation number, and coordination geometry), and that of the axial ligand on the central metal ion. The external factors cover acid-base equilibrium, oxidation and reduction on the macrocycle, aggregation and dimerization (exciton coupling and π–π interaction), and solvent effects. In particular, much attention is focused on aggregation and acid-base equilibrium because these phenomena are frequently misunderstood.

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Notes

  1. 1.

    The appearance of such an intense band in this spectral region is unusual. The origin of this band is discussed in Sect. 3.2.2.1.

  2. 2.

    Although it is generally known that the Q-band position of phthalocyanines does not strongly depend on the metal ion in the cavity of the macrocycle (Sect. 3.2.1), the presence of a pnictogen can give rise to a significant redshift of the Q-band [2–11].

  3. 3.

    Little structural deformation of the macrocyclic ligand has been found in its crystal structure.

  4. 4.

    Effects of peripheral substituents on the absorption spectra are discussed in Sect. 4.2.2.

  5. 5.

    The width of the Q-band is large. Only the absorption maximum wavelength is reported in the literature.

  6. 6.

    For the BiIII derivatives, the dissociation of axial ligands in solutions has been suggested from electrochemical data [2, 3].

  7. 7.

    Although the authors of Ref. [58] have identified their compounds as [P(Pc)(OH)2]OH in their report, a neutral composition is considered more likely on the basis of experimental lines of evidence provided in the later report [57]. Note that both papers reported the same tetra-tert-butyl derivative.

  8. 8.

    Protonation at meso nitrogen atom(s) gives rise to a significant redshift and splitting of the Q-band (Sect. 3.2.5.2).

  9. 9.

    The MLCT transition can be understood as the simultaneous occurrence of metal-centered oxidation, FeII to FeIII, and ligand-centered reduction, pc2− to pc3−. In contrast, LMCT can be understood as the simultaneous occurrence of metal-centered reduction and ligand-centered oxidation [47].

  10. 10.

    Derivatives of lead and bismuth with a higher oxidation state are unknown.

  11. 11.

    Refer to Sect. 1.1.4 for the definition of HOMO and LUMO.

  12. 12.

    A sharp Faraday A-term is observed in each corresponding MCD spectrum.

  13. 13.

    Note that the fusion of benzo groups to the periphery of TAP derivatives (i.e., ring expansion from TAP to Pc) contributes not only to the expansion of the π-conjugation system but also to enhancing the imbalance between the two highest occupied frontier orbitals (a1u and a2u). See Sect. 2.2.7.

  14. 14.

    It has been mentioned in Sect. 3.2.3.2 that the appearance of a single Q-band for the structural intermediate of the phthalocyanine and naphthalocyanine derivatives (compound 2 in Fig. 3.12 righy) was predicted using SAP theory.

  15. 15.

    As mentioned in Sect. 2.2.8, the intensity of B-terms is larger as the two excited states are closer in energy.

  16. 16.

    States can be degenerate when the molecular symmetry is not lower than C3.

  17. 17.

    Only monomers and dimers contribute to the absorption spectra (Fig. 3.14) within this concentration range because sharp isosbestic points are seen in the spectral changes; hence, the two species are in equilibrium.

  18. 18.

    The author has learned through his activities as a scientist and an article reviewer that a considerable number of people (including experts) believe that highly aggregating phthalocyanines are poorly soluble in common solvents or that highly soluble phthalocyanines are nonaggregating. However, this is not always true. For example, the octa(alkynyl)-substituted derivative in Fig. 3.14 is highly soluble (its solubility reaches almost 10−2 M) but it also aggregates even in dilute solutions (ca. 10−5 M) as illustrated above. On the other hand, the SbV complex of unsubstituted Pc is not very soluble (at most, 10−4 M) whereas its aggregation could not be detected by optical absorption spectroscopy using an optical cell of 1 mm path length up to the upper limit of the concentration range studied. Thus, having good solubility is one thing and being nonaggregating is another, at least with respect to phthalocyanines.

  19. 19.

    J-aggregates show their main band at a red flank of the monomer band, but the converse is not necessarily true. A number of phthalocyanines show an additional band at a wavelength longer than that of the monomer Q-band owing to acid-base equilibria involving the macrocycle (Sect. 3.2.5.2), electron transfer (Sect. 3.2.6.1), etc. Special care has to be taken when assigning such extra bands at longer wavelengths as “J-aggregates” particularly in the case of nondonor solvents (Sect. 3.2.5.2).

  20. 20.

    Readers are reminded that the Lambert-Beer plot must include the zero point because the absorbance attributed to the compound must be zero when its concentration is zero. Nevertheless, a number of authors have concluded a lack of aggregation of their compounds on the basis of the linear Lambert-Beer plot within a narrow concentration range excluding the zero point. The same plot including the zero point could be nonlinear.

  21. 21.

    Actually, this is the distance between the planes composed of the four pyrrole nitrogen atoms in each macrocyclic ligand.

  22. 22.

    The splitting of the Q-band can be explained by exciton coupling (one is assigned as an allowed transition and the other weaker one is due to the forbidden transition that borrowed intensity from vibronic transition). However, the increase in the magnitude of the splitting with decreasing ionic radius is much steeper than expected from the change in the interplanar distance (Eq. 3.1).

  23. 23.

    This model also successfully explains the spectral properties of a series of lanthanoid(III) derivatives of neutral double-decker phthalocyanines [M(pc2−)(pc−)] and [M(pc−)] +2 as well as their redox potentials.

  24. 24.

    In these works, the authors have tried to explain the splitting on the basis of the exciton coupling alone.

  25. 25.

    The authors reported that the absorption spectra of the Si–Si dimers are very similar to those of tetrabenzotriazacorroles (Sect. 3.3.3).

  26. 26.

    We do not consider protonation at peripheral substituents or axial ligands because they are far from the innermost 16-membered ring, and detectable spectral changes are unlikely to be observed. An example of spectral changes associated with protonation at the axial ligand has been described elsewhere (Sect. 3.2.1; Fig. 3.3).

  27. 27.

    See Sect. 1.2.2 for the representation of Pc(2-).

  28. 28.

    Singly oxidized phthalocyanines are more prone to molecular aggregation than unoxidized species [101, 128, 193].

  29. 29.

    SOMO = singly occupied molecular orbital. In this context, this means the HOMO from which one electron has been removed by oxidation.

  30. 30.

    Note that the formal representation, pc(2-) and pc(-), used to denote oxidation states of the macrocyclic ligands is not appropriate in this case because their π conjugation systems are not independent of each other (Sect. 3.2.4.6). However, we adopt this conventional formulation instead of pc2(3-) to avoid unnecessary confusion.

  31. 31.

    The Q-band of the heteroleptic dimer has been found to be degenerate on the basis of an MCD study [206, 208].

  32. 32.

    Decreasing interplanar distance gives rise to stronger π–π interaction between the two macrocycles and hence the splitting between b1 and a2 orbitals (Sect. 3.2.4.6).

  33. 33.

    The pc(3-) species are referred to as radical anions for the same reason as in the case of singly oxidized phthalocyanine pc(1-).

  34. 34.

    As this complex has a six-coordinate, octahedral geometry (the two cyanide ions are in trans positions above and below the phthalocyanine macrocyclic ligand) [223], it is convenient for investigating the effects of the solvent on the electronic transition in the macrocyclic ligand alone for the following reasons: (1) donor-solvent molecules are unlikely to coordinate to the central metal ion because of the crowded coordination geometry around the metal ion; (2) ligand substitution is unlikely to occur because of strong Co–CN and Co–N(phthalocyanine) bonding; (3) the presence of the axial ligands and the net negative charge of the complex itself should prevent the aggregation of the macrocyclic ligands owing to steric hindrance and electrostatic repulsion, respectively; (4) it has no axial ligand or peripheral substituent that can be involved in the chemical interaction, such as hydrogen bonding, with the surrounding solvent molecules.

  35. 35.

    Plots of the Q-band position only in nondonor solvents exhibit a fairly good linear correlation.

  36. 36.

    Note that the addition of salicylic acid did not change the Q-band position [224].

  37. 37.

    The MnII species fails to react with oxygen when dissolved in highly purified dry pyridine [49].

  38. 38.

    Because of the free rotation around the Si–O–Si axis, there can be more than one rotational isomer based on the difference in the torsion angle between the macrocyclic ligands.

  39. 39.

    The tilted stacking of the phthalocyanine rings with respect to the Si–O–Si axis gives rise to an oblique conformation between the two macrocyclic ligands (Fig. 3.19c).

  40. 40.

    The same compound is shown in Fig. 3.3 and has been found to be free from aggregation in ethanolic solution [30, 31].

  41. 41.

    An aggregation phenomenon would give a convex curve (see Fig. 3.14 inset, for example) in the Lambert-Beer plot.

  42. 42.

    The metal-free triazacorrole derivatives (corrolazines) and their transition metal complexes are known [for example, 245, 246]. Note that the phosphorus complexes of tetrabenzocorrolazine used to be considered as PIII derivatives of phthalocyanines (which are still unknown).

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Isago, H. (2015). Real Optical Absorption Spectra Observed in Laboratories. In: Optical Spectra of Phthalocyanines and Related Compounds. NIMS Monographs. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55102-7_3

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