1,5-Diisocyanonaphthalene
Chemical compound
From Wikipedia, the free encyclopedia
1,5-Diisocyanonaphthalene (DIN) is an aromatic diisocyanide (isonitrile) in which two âNâ¡C groups occupy the 1- and 5-positions of the naphthalene ring. The compound is also named 1,5-naphthalenediyldiisocyanide and has the molecular formula C12H6N2 and relative molar mass 178.19 g/mol.[1] It has been studied as a photophysical probe and as a lead compound for antifungal research.
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| Names | |
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| Preferred IUPAC name
1,5-Diisocyanonaphthalene | |
| Other names
DIN; 1,5-naphthalenediyldiisocyanide | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| C12H6N2 | |
| Molar mass | 178.194 g·molâ1 |
| Appearance | Solid |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards |
Laboratory chemical; handle with standard precautions |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Structure and properties
Isocyanides feature the âNâ¡C functional group (often depicted as âN+â¡Câ â âN=C:), bonded to the aromatic ring through nitrogen. DIN's two isocyanide substituents make it a rigid, weakly polar Ï-system. Photophysically, DIN shows limited solvatochromism compared with mono-formamido/mono-isocyano analogues (e.g., ICNF), but it forms notable Ï-complexes with aromatic solvents that modulate emission, enabling discrimination among aromatics by fluorescence.[2]
Synthesis
1,5-Diisocyanonaphthalene can be obtained by converting 1,5-diaminonaphthalene to the corresponding N,Nâ²-diformamide, followed by dehydration (e.g., with phosphorus oxychloride in the presence of base). Reaction conditions and solvent choice influence outcome for this system.[3]
Applications
Fluorescence/analytical: DIN's emission responds to specific ÏâÏ interactions in aromatic solvents, suggesting use in distinguishing aromatic hydrocarbons optically; related hydrolysis-derived ICNF is a strongly solvatochromic dye.[2]
Antifungal activity
In standardized CLSI broth microdilution tests against three Aspergillus fumigatus strains (MYA 3627, ATCC 204305 and Af293), 1,5-diisocyanonaphthalene showed the lowest MIC values among the tested isocyano-naphthalene derivatives, namely 0.6 μg/mL (3.4 μM) for all strains. Practical use may be limited by poor aqueous solubility; a related dimethylamino analogue (DIMICAN) progressed to in-vivo evaluation in a murine aspergillosis model.[4]