Tetrabutylammonium triiodide

Last updated
Tetrabutylammonium triiodide
Tetrabutylammonium triiodide.svg
Names
IUPAC name
Tetrabutylazanium triiodide
Other names
TBAI3
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C16H36N.I3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1
    Key: SBSSZSCMFDYICE-UHFFFAOYSA-N
  • CCCC[N+](CCCC)(CCCC)CCCC.I[I-]I
Properties
C16H36I3N
Molar mass 623.184 g·mol−1
AppearanceBlack powder
Melting point 69–71 °C (156–160 °F; 342–344 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H319
P264, P264+P265[ ? ], P280, P302+P352, P305+P351+P338, P321, P332+P317[ ? ], P337+P317[ ? ], P362+P364
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetra-n-butylammonium triiodide (TBAI3) is a quaternary ammonium salt with a triiodide counterion. It is a common carrier of the triiodide used in chemical synthesis of photovoltaic materials, [2] organic conductors and superconductors. [3] In crystals, the triiodide moieties are linear and shows high crystallinity. [4] [5] The crystals have a black appearance with a needle or plate-like habit.

See also

Related Research Articles

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<span class="mw-page-title-main">Sodium hydride</span> Chemical compound

Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong yet combustible base in organic synthesis. NaH is a saline (salt-like) hydride, composed of Na+ and H ions, in contrast to molecular hydrides such as borane, methane, ammonia, and water. It is an ionic material that is insoluble in organic solvents (although soluble in molten Na), consistent with the fact that H ions do not exist in solution. Because of the insolubility of NaH, all reactions involving NaH occur at the surface of the solid.

<span class="mw-page-title-main">Triiodide</span> Ion

In chemistry, triiodide usually refers to the triiodide ion, I
3
. This anion, one of the polyhalogen ions, is composed of three iodine atoms. It is formed by combining aqueous solutions of iodide salts and iodine. Some salts of the anion have been isolated, including thallium(I) triiodide (Tl+[I3]) and ammonium triiodide ([NH4]+[I3]). Triiodide is observed to be a red colour in solution.

Tetra-<i>n</i>-butylammonium fluoride Chemical compound

Tetra-n-butylammonium fluoride, commonly abbreviated to TBAF and n-Bu4NF, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F. It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents.

<span class="mw-page-title-main">Pentacene</span> Hydrocarbon compound (C22H14) made of 5 fused benzene rings

Pentacene is a polycyclic aromatic hydrocarbon consisting of five linearly-fused benzene rings. This highly conjugated compound is an organic semiconductor. The compound generates excitons upon absorption of ultra-violet (UV) or visible light; this makes it very sensitive to oxidation. For this reason, this compound, which is a purple powder, slowly degrades upon exposure to air and light.

<span class="mw-page-title-main">18-Crown-6</span> Chemical compound

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<span class="mw-page-title-main">Metal–organic framework</span> Class of chemical substance

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The polyiodides are a class of polyhalogen anions composed entirely of iodine atoms. The most common and simplest member is the triiodide ion, I
3
. Other known larger polyiodides include [I4]2−, [I5], [I6]2−, [I7], [I8]2−, [I9], [I10]2−, [I10]4−, [I11]3−, [I12]2−, [I13]3−, [I14]4-, [I16]2−, [I22]4−, [I26]3−, [I26]4−, [I28]4− and [I29]3−. All these can be considered as formed from the interaction of the I, I2, and I
3
building blocks.

<span class="mw-page-title-main">Solid</span> State of matter

Solid is one of the four fundamental states of matter. The molecules in a solid are closely packed together and contain the least amount of kinetic energy. A solid is characterized by structural rigidity and resistance to a force applied to the surface. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire available volume like a gas. The atoms in a solid are bound to each other, either in a regular geometric lattice, or irregularly. Solids cannot be compressed with little pressure whereas gases can be compressed with little pressure because the molecules in a gas are loosely packed.

Covalent organic frameworks (COFs) are a class of materials that form two- or three-dimensional structures through reactions between organic precursors resulting in strong, covalent bonds to afford porous, stable, and crystalline materials. COFs emerged as a field from the overarching domain of organic materials as researchers optimized both synthetic control and precursor selection. These improvements to coordination chemistry enabled non-porous and amorphous organic materials such as organic polymers to advance into the construction of porous, crystalline materials with rigid structures that granted exceptional material stability in a wide range of solvents and conditions. Through the development of reticular chemistry, precise synthetic control was achieved and resulted in ordered, nano-porous structures with highly preferential structural orientation and properties which could be synergistically enhanced and amplified. With judicious selection of COF secondary building units (SBUs), or precursors, the final structure could be predetermined, and modified with exceptional control enabling fine-tuning of emergent properties. This level of control facilitates the COF material to be designed, synthesized, and utilized in various applications, many times with metrics on scale or surpassing that of the current state-of-the-art approaches.

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4
, found in potassium molybdate up to extremely large structures found in isopoly-molybdenum blues that contain for example 154 Mo atoms. The behaviour of molybdenum is different from the other elements in group 6. Chromium only forms the chromates, CrO2−
4
, Cr
2
O2−
7
, Cr
3
O2−
10
and Cr
4
O2−
13
ions which are all based on tetrahedral chromium. Tungsten is similar to molybdenum and forms many tungstates containing 6 coordinate tungsten.

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Cerium(III) iodide (CeI3) is the compound formed by cerium(III) cations and iodide anions.

<span class="mw-page-title-main">Contorted aromatics</span>

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<span class="mw-page-title-main">Linear chain compound</span> Materials made of one-dimensional arrays of metal-metal bonded molecules

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The telluride oxides or oxytellurides are double salts that contain both telluride and oxide anions. They are in the class of mixed anion compounds.

References

  1. "Tetrabutylammonium triiodide". pubchem.ncbi.nlm.nih.gov. Retrieved 31 March 2022.
  2. Starkholm, Allan; Kloo, Lars; Svensson, Per H. (2019-01-28). "Polyiodide Hybrid Perovskites: A Strategy To Convert Intrinsic 2D Systems into 3D Photovoltaic Materials". ACS Applied Energy Materials. 2 (1): 477–485. doi:10.1021/acsaem.8b01507. S2CID   139565235.
  3. Shibaeva, Rimma P.; Yagubskii, Eduard B. (2004-11-01). "Molecular Conductors and Superconductors Based on Trihalides of BEDT-TTF and Some of Its Analogues". Chemical Reviews. 104 (11): 5347–5378. doi:10.1021/cr0306642. ISSN   0009-2665. PMID   15535653.
  4. Herbstein, F. H.; Kaftory, M.; Kapon, M.; Saenger, W. (1981-01-01). Herbstein, F. H.; Kaftory, M.; Kapon, M.; Saenger, W. (eds.). "Structures of three crystals containing approximately — linear chains of triiodide ions". Zeitschrift für Kristallographie - Crystalline Materials. 154 (1–2): 11–30. Bibcode:1981ZK....154...11H. doi:10.1524/zkri.1981.154.1-2.11. ISSN   2194-4946.
  5. Brotherton, Wendy S.; Clark, Ronald J.; Zhu, Lei (2012-08-03). "Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion". The Journal of Organic Chemistry. 77 (15): 6443–6455. doi:10.1021/jo300841c. ISSN   0022-3263. PMID   22780866.