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Gallium monoiodide

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Gallium monoiodide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/Ga.HI/h;1H/q+1;/p-1
    Key: LRPWSMQGXLANTG-UHFFFAOYSA-M
  • [Ga]I
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gallium monoiodide is an inorganic gallium compound with the formula GaI or Ga4I4. It is a pale green solid and mixed valent gallium compound, with gallium in the +1 and +3 oxidation states. It is used as a pathway for many gallium-based products. Unlike the gallium(I) halides first crystallographically characterized,[1] gallium monoiodide has a more facile synthesis and allowing a synthetic route to many low-valent gallium compounds.

Synthesis

In 1990, Malcolm Green synthesized gallium monoiodide by the ultrasonication of liquid gallium metal with iodine in toluene yielding a pale green powder referred to as gallium monoiodide.[2] The chemical composition of gallium monoiodide was not determined until the early to mid-2010s despite its simple synthesis.

In 2012, the pale green gallium monoiodide was determined to be a combination of gallium metal and gallium(I,III) iodide, having the chemical composition [Ga0]2[Ga+][GaI4−].[3] However, in 2014, it was found that the incomplete reaction of gallium metal with iodine yielded gallium monoiodide with this chemical composition. Gallium monoiodide synthesized with longer reaction times for complete reaction had a different chemical composition [Ga0]2[Ga+]2[Ga2I62-].[4]

The resultant gallium monoiodide is highly air sensitive, but stable under inert atmosphere conditions for up to a year at -35 ˚C.[4]

Characterization

The chemical composition of gallium monoiodide has been probed with FT-Raman spectroscopy, powder X-ray diffraction, NMR spectroscopy and nuclear quadrupole resonance.[4][3][5] It was proposed that gallium monoiodide is a combination of gallium(0) metal, Ga2I3 and Ga2I4 based on the characteristic Raman spectra of these constituents.[5] This hypothesis was confirmed as two variants of gallium monoiodide were determined to have the chemical compositions [Ga0]2[Ga+][GaI4−], simplified as Ga2I4·2Ga, and [Ga0]2[Ga+]2[Ga2I62-], simplified as Ga2I3·Ga.[4][3]

[Ga0]2[Ga+][GaI4−]

When probed by NMR spectroscopy, gallium monoiodide with chemical composition [Ga0]2[Ga+][GaI4−] showed the presence of liquid gallium metal rather than solid gallium metal.[3] When probed by 127I NQR,[4] it showed the presence of Ga2I4 and further confirms the [Ga0]2[Ga+][GaI4−] assignment.[6] Raman spectroscopy has also confirmed this composition assignment. [4][7][4] All of the evidence from other spectroscopic methods, and power x-ray diffraction patterns, the assignment of [Ga0]2[Ga+][GaI4−] for this gallium monoiodide variant was validated.

[Ga0]2[Ga+]2[Ga2I62-]

When probed by 127I NQR, three peaks were observed at 106.35, 107.83, and 123.54 MHz, which align with the assignment to Ga2I3.[4] Raman spectroscopy has also confirmed this assignment with vibrational frequencies at 124 (strong), 292 (weak) and 188 (weak) cm−1.[4] These frequencies align with those from a Ga4I6 reference.[7] Finally, power x-ray diffraction supports that this gallium monoiodide variant matches that of characteristic Ga2I3, which is different from that of GaI2.[4]

69/71Ga SSNMR of gallium monoiodide

There have been some conflicting reports in interpreting the 69/71Ga solid-state NMR spectra of the two gallium monoiodide variants. One interpretation is that a signal at δiso = -424(5) ppm with a non-zero QI tensor is characteristic of a distorted tetrahedral [GaI4−] constituent.[3] Thus, this spectra would defend a [Ga0]2[Ga+][GaI4−] assignment. However, another finding shows that this signal at δiso = -425(3) is seen in conjunction with another peak at δiso = 15(5) ppm. In this case, the peak at δiso = -425(3) could correspond to Ga+ as seen within GaI2, and δiso = 15(5) ppm could correspond to [Ga2I62-].[4] Thus, this spectra could also defend a [Ga0]2[Ga+]2[Ga2I62-] assignment. These differing interpretations suggest that 69/71Ga solid-state NMR alone will not be able to conclusively assign a specific chemical composition to a gallium monoiodide variant. 69/71Ga solid-state NMR should be analyzed in conjunction with other spectroscopic measurements to make these assignments robust.

[Ga0]2[Ga+][GaI4−] can convert to [Ga0]2[Ga+]2[Ga2I62-] over time.[4]

Reactivity

While there is some discrepancy with how these different gallium monoiodide variants are obtained (i.e. length of reaction, temperature of reaction, time of degradation), the fact that two different gallium monoiodide variants can be accessed provides some insight into how such a wide range of reactivities can be accessed.

Gallium monoiodide is used as a precursor for a variety of reactions. Early-on, gallium monoiodide was shown to access alkylgallium diiodides via oxidative addition by reacting liquid gallium metal and iodine in the presence of an alkyl iodide, RI.[1][2][8] Since then, other organogallium complexes have been accessed, as well as Lewis base adducts and gallium based clusters.[8] Some of these chemistries are explained in further detail below.

Ga Lewis base adducts

Reaction pathways of various gallium monoiodide Lewis base adducts. Reactions were conducted in toluene at - 78 ˚C.[9] (L = phosphines, ethers, amines).[8][9] Image adapted from Baker and coworkers.[8]

Gallium monoiodide can react with a wide range of monodentate Lewis bases to form Ga(II), Ga(III), or mixed valent compounds, as well as gallium-based dimers and trimers. For example, gallium monoiodide can react with primary, secondary, and tertiary amines, secondary or tertiary phosphines or ethers to form Ga(II)-Ga(II) dimers.[2][8][10] Gallium monoiodide can also react with PPh3 to form a Ga(III)I3PPh3 complex.[2] It can also react with a less sterically encumbered PEt3 ligand to form a Ga(II)-Ga(I)-Ga(II) mixed valent complex with datively coordinated PEt3 ligands.[8][10] While the exact composition of the gallium monoiodide starting material from which these adducts are derived is uncertain, it is believed that these reactions occur via disproportionation given that solid Ga metal is deposited upon reaction.[9]

Interestingly, when gallium monoiodide reacts with SbPh3 in similar reaction conditions as with the PPh3 ligand, we observe a SbPh3 fragment datively bonded to a GaPhI2 fragment.[11] The difference in reactivity between PPh3 and SbPh3, a heavy atom analogue of PPh3, can be attributed to a weaker Sb-C bond, allowing for transfer of a phenyl group from antimony to gallium. This suggests that gallium monoiodide can be used as a reducing agent as well.[8][11]

Reaction of gallium monoiodide and SbPh3 yields a complex with the SbPh3 ligand datively bonded to GaPhI2. Image adapted from Baker and coworkers.[8]

When N-heterocyclic carbenes were reacted with gallium monoiodide, only a sterically encumbered IPr ligand was shown to form a Lewis base adduct.[9] However, as described below, gallium monoiodide has been shown to react with diazabutadienes and subsequent reduction by potassium metal to form Ga analogues of NHCs.[8] Other Ga based carbenes can be accessed from a gallium monoiodide precursor using Li[nacnac].[8]

While monodentate Lewis bases form Ga adducts that access a wide range of Ga oxidation states, when gallium monoiodide reacts with multidentate Lewis bases, Ga(III) complexes are predominantly formed. This reactivity has been probed with bipyridine (bipy), phenyl-terpyridine (Phterpy), and bis(imino)pyridine (bimpy) ligands, all of which have yielded Ga(III) complexes.[8][12] Crystallographically, the bipy derivative has been shown to adopt a distorted octahedral geometry, with a Ga–N bond length of 2.063 Å. The Phterpy derivative adopts a distorted trigonal bipyramidal geometry where the two equatorial Ga–N bonds (as drawn) are longer than the axial Ga-N bond, with 2.104 Å and 2.007(5) Å bond lengths respectively. The average Ga-N bond length (2.071 Å) has been shown to be similar to that of a neutral GaCl3(terpy) Lewis base adduct (2.086 Å).[13] The bimpy derivative is described as having a distorted square-based pyramidal geometry. Like for the Phterpy derivative, the equatorial imino Ga-N bonds (2.203 Å) were found to be longer than the axial pyridyl Ga-N bond (2.014(7) A˚).[12] Despite these similar reactivities and bond characteristics, when gallium monoiodide was reacted with imino-substituted pyridines (RN=C(H)Py), unique reactivity was observed. Reductive coupling of the imino-substituted pyridines formed diamido-digallium(III) complexes.[12] Such reactivity points toward the usefulness of gallium monoiodide precursors in organic synthesis, given the formation of new C-C bonds.

Reaction pathways with gallium monoiodide and polydentate Lewis bases form Ga(III) salts (R = Ar, But; Ar = C6H3Pri2-2,6; Py = 2-pyridyl). Reactions were conducted in toluene at - 78 ˚C. Only the bimpy derivative was reacted at 25 ˚C. All complexes have been crystallographically characterized. Image adapted from Baker and coworkers.[12]

Ga heterocycles

Gallium monoiodide can also be used as a precursor to form gallium-based heterocycles. Reactions with diazabutadienes, {RN=C(H)}2, can form monomers or dimers based on the substituents on the diazabutadienes. More sterically hindered substituents such as But have resulted in the formation of Ga(II) dimers, whereas reactions with alkyl or aryl substituted diazabutadienes have formed Ga(III) monomers.[8] Two equivalents of gallium monoiodide can be reacted with phenyl-substituted 1,4-diazabuta-1,3-dienes to form a Ga heterocycle with a diazabutadiene monoanion.[14] EPR spectroscopy has revealed that the diazabutadiene fragment is a paramagnetic monoanionic species rather than an ene-diamido dianion or a neutral ligand.[14] Thus, gallium monoiodide undergoes a disproportionation reaction to form a Ga(III) complex with deposition of a Ga(0) metal.[8][14] Upon further reaction with a 1,4-dilithiated diazabutadiene, this Ga heterocycle forms a new complex with the diazabutadiene monoanion fragment datively bonded (Ga-N bond lengths 1.9678(13) Å) to the Ga center and an ene-diamido dianion covalently bonded (Ga-N bond lengths 1.8831(13) Å) to the Ga center.[14] The geometry about the Ga center suggests that the electrons in the two diazabutadiene systems do not delocalize across the entire complex.

Ga heterocycles formed from the reaction of gallium monoiodide with 1,4-diazabuta-1,3-dienes. R = 2,6-dimethylphenyl; 2,4,6-trimethylphenyl; 2,6-diisopropylphenyl. For the 1,4-dilithiated diazabutadiene reagent, R = 2,6-dimethylphenyl. Image adapted from Pott and coworkers.[14]

One very important reactivity of this Ga(III) heterocycle is its ability to access gallium analogues of N-heterocyclic carbenes upon reduction with potassium metal.[15] Although a gallium analogue of N-heterocyclic carbenes had been synthesized previously,[16] having access to heavier analogues of N-heterocylic carbenes from a synthetically more facile gallium monoiodide route has opened new avenues in coordination chemistry, such as access to new Ga-M bonds.[17][18][19]

Gallium monoiodide can also be used to access six-membered Ga(I) heterocycles that have parallels to gallium analogues of N-heterocyclic carbenes. These neutral Ga(I) heterocycles can be synthesized by reacting gallium monoiodide and Li[nacnac].[18][20]

Reaction of gallium monoiodide (slurry) and Li[nacnac] in a dry ice/acetone bath to access a Ga(I) heterocycle. Excess potassium metal can be added to circumvent a Ga(II) derivative of the six-member Ga(I) heterocycle.[20] Ar = Dipp. Image adapted from Baker and coworkers.[18]

GaCp and GaCp*

Another interesting reaction with gallium monoiodide has been the facile access to half-sandwich complexes, GaCp* and GaCp. Schnöckel first accessed hexameric GaCp* using more synthetically difficult routes.[21] However, Jutzi and coworkers showed that GaCp*, a heavily employed ligand for transition metal complexes, can be accessed more simply by reacting gallium monoiodide with a potassium salt of the desired ligand.[22] To avoid benzyl iodide side products, both the gallium monoiodide and the GaCp* ligand have been synthesized in benzene rather than toluene.[8][22] Using this methodology, both Cp*Ga and (C5Me4Et)Ga have been synthesized cleanly under more practical reaction conditions.

Furthermore, Schenk and coworkers showed that GaCp, which is less sterically hindered than GaCp*, can also be accessed using a gallium monoiodide precursor. This ligand can be synthesized with a metathesis reaction of NaCp with gallium monoiodide.[23] This GaCp ligand has been used to access a GaCp2I complex with datively bonded GaCp. This complex showcases an uncommon donor-acceptor Ga-Ga bond. GaCp can also be used to access a Lewis acid B(C6F5)3 complex with a datively bonded GaCp.[23] For both of these two complexes, the GaCp* analogues have been synthesized and x-ray crystallography has supported that, as expected, GaCp* is a slightly stronger donor than GaCp.

GaCp reacts with Cr(CO)5(cyclooctene) to form a new CpGa–Cr(CO)5. The GaCp* analogue can also be accessed. Image drawn based on crystallographic data from Naglav and coworkers.[24]

Like GaCp*, GaCp can also coordinate to transition metal complexes such as Cr(CO)5(cyclooctene) or Co2(CO)8 to yield CpGa–Cr(CO)5 or (thf)GaCp{Co(CO)4}2.[24] For CpGa–Cr(CO)5, the Ga-Cr bond length (239.6 pm) is similar to that for a GaCp* analogue (240.5 pm). For this complex, the trans effect is also observed, where the Cr-CO bond trans to the GaCp ligand is contracted (186 pm) relative to the cis Cr-CO bonds (189.5 pm). While GaCp can act as a terminal ligand similar to GaCp*, it was determined that GaCp analogues react faster than their GaCp* counterparts. This can be attributed to the lower steric bulk of GaCp, and Naglav and coworkers have suggested that working at lower temperatures can help access stable complexes with GaCp ligands.[24]

Unlike reactivity with Cr(CO)5(cyclooctene), reactivities of GaCp* and GaCp with Co2(CO)8 diverge significantly.[24] Dicobalt octacarbonyl, or Co2(CO)8, exists in various isomeric states. One such isomer contains two bridging CO ligands. When GaCp* reacts with Co2(CO)8, two equivalents of CO gas are released, forming (CO)3Co[μ2-(η5-GaCp*)]2-Co(CO)3. This is a derivative of the dicobalt octacarbonyl complex where the bridging CO moieties are replaced by bridging GaCp* moieties.[25] On the other hand, GaCp enables oxidative addition to Co2(CO)8 to form (thf)GaCp{Co(CO)4}2, where gallium has sigma interactions to two Co(CO)4 units. The average Ga–Co bond length is 248.5 pm and gallium is in a formally +3 oxidation state in this new complex.[25] Overall, straightforward synthesis of GaCp from a gallium monoiodide precursor has many merits in expanding the scope of transition metal chemistry with lower valent species.

Gallium clusters

Examples of Ga clusters synthesized from variants of gallium monoiodide starting materials. R = Si(SiMe3)3. For the [Ga9{Si(SiMe3)3}6]− cluster, the polyhedral vertices are all Ga. Reactions were conducted in toluene at -78 ˚C. Image adapted from (top) Linti and coworkers[26] and (bottom) Kostler and coworkers.[27]

A variety of gallium clusters have also been synthesized from a gallium monoiodide precursor. Many gallium-based clusters have been previously synthesized from GaX precursors as prepared by Schnöckel and coworkers.[28] However, new clusters have also been prepared with the more easily accessible gallium monoiodide starting material. These clusters have often been isolated as salts with bulky silyl or germyl anions, such as [Si(SiMe3)3]−.[8] An example of an isolated gallium cluster is [Ga9{Si(SiMe3)3}6]−, which has a pentagonal bipyramidal polyhedral structure. It is synthesized by reacting gallium monoiodide with Li(thf)3Si(SiMe3)3 in toluene at -78 ˚C.[8][27] This reaction has been shown to access a wide array of products, which may be attributed to the wide range of gallium monoiodide compositions that have been subsequently probed by Malbrecht and coworkers. Of these products, [Ga9{Si(SiMe3)3}6]− is especially unique because Ga was found to have a very low average oxidation state (0.56) and also because this cluster has fewer R substituents than polyhedron vertices.[27] Other clusters that been isolated via similar reaction pathways include [Ga10{Si(SiMe3)3}6], which is a conjuncto-polyhedral cluster, and a closo-silatetragallane anion, which contains three 2-electron-2-center and three 2-electron-3-center bonds.[8][29][26] Interestingly, this latter species can only be synthesized when sub-stoichiometric quantities of I2 are utilized to access a "Ga2I3" intermediate species.[26] This is equivalent to reacting liquid gallium metal and iodine to pre-completion, which, as explained above, accesses the [Ga0]2[Ga+]2[Ga2I62-] variant of gallium monoiodide. This highlights the versatility of the gallium monoiodide precursor in accessing a wide range of gallium-based complexes.

Reaction of a diaryl Co(II) precursor with gallium monoiodide yields a nido-type Co-GaI cluster. Ellipsoids set at 50% probability. Grey = carbon, blue = cobalt, pink = gallium, and magenta = iodine. Hydrogens not depicted. Image recreated using .cif file (deposited to The Cambridge Structural Database) obtained by Blundell and coworkers.[30]

Gallium monoiodide can also form cluster-type compounds with transition metals precursors. One example is the reaction between gallium monoiodide and (2,6-Pmp2C6H3)2Co, (Pmp = C6Me5), which yields a nido-type cluster.[30] This molecule has been described as being similar to a cubane, where the corners are metal and bridging iodine atoms, with one corner removed. This is a particularly unique Co-GaI cluster due to its unusual geometry for transition metal compounds containing heavy group 13 atoms such as gallium. The bond critical points and bond paths, as computed with QTAIM analysis, support that while there are Co-Ga bonds, there are no Ga-Ga bonds.[30]

Bond critical points and bond paths of a Co-GaI cluster. Image reproduced from Blundell and coworkers[30] using Multiwfn 3.8 software.[31]

Finally, gallium monoiodide has been able to form clusters with heavy gold atoms by acting as a reducing reagent when combined with GaCp* and LAuX (i.e. AuI(PPh3) or AuCl(PPh3)).[8][32] This cluster contained the first crystallographically confirmed Ga-Au bonds. Based on the bond critical points of the Ga-Au and Au-Au bonds of this cluster, as well as NBO analysis of atomic charges, it was determined that this cluster could be best described as a Au3 cluster ligated by Ga ligands. In addition, NBO analysis showed that the charge on the galliums within the GaCp* ligands were much higher than the charge on the Au atoms and the charge on the gallium atoms within the GaI2 motifs. This suggests that non-bridging Ga-Au bonds are highly polarized, whereas the µ-bridging Ga-Au bonds are more non-polar covalent in character.[32] While gallium cluster chemistry has been explored in great detail, being able to access clusters with the more tractable gallium monoiodide precursor may allow the discovery of new species that cannot be accessed from other GaX precursors.

Ga-Au cluster formed by dropwise addition of LAuX to a mixture of GaCp*/"GaI" (excess) in dichloromethane. Image adapted from Anandhi and coworkers.[32]

See also

References

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