lophine
{{Chembox
| ImageFile = Lophine.svg
| ImageSize = 110px
| ImageAlt =
| IUPACName =
| OtherNames = 2,4,5-triphenylimidazole
|Section1={{Chembox Identifiers
| CASNo = 484-47-9
| ChEMBL = 34173
| ChemSpiderID = 9815
| EC_number = 207-606-6
| PubChem = 10232
| UNII = Q6K46G80ZD
| StdInChI=1S/C21H16N2/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)23-21(22-19)18-14-8-3-9-15-18/h1-15H,(H,22,23)
| StdInChIKey = RNIPJYFZGXJSDD-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)C2=C(N=C(N2)C3=CC=CC=C3)C4=CC=CC=C4
}}
|Section2={{Chembox Properties
| C = 21|H=16|N=2
| MolarMass =
| Appearance = white solid
| Density = 1,0874 g/cm3
| MeltingPtC = 275
| MeltingPt_notes =
| BoilingPt =
| BoilingPt_notes =
| Solubility = }}
|Section3={{Chembox Hazards
| GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/10232#section=Safety-and-Hazards]
| GHSPictograms = {{GHS06}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301}}
| PPhrases = {{P-phrases|264|270|301+316|321|330|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Lophine is the organic compound with the formula {{chem2|(C6H5C)2N2HCC6H5}}. It is a derivative of imidazole wherein all three carbon atoms have phenyl groups as substituents. A white solid, this compound gave the first example of chemiluminescence when its basic solutions were exposed to air.{{cite journal |doi=10.1002/cber.18770100122 |title=Untersuchungen über Hydrobenzamid, Amarin und Lophin |date=1877 |last1=Radziszewski |first1=B. R. |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=10 |pages=70–75 |url=https://zenodo.org/record/1425132 }} Its chemiluminescence continues to attract attention.{{cite journal |doi=10.1002/bmc.226 |title=Lophine derivatives as versatile analytical tools |date=2003 |last1=Nakashima |first1=Kenichiro |journal=Biomedical Chromatography |volume=17 |issue=2–3 |pages=83–95 |pmid=12717796 }}
Lophine and its dihydro analogue amarine (meso-2,4,5-triphenyl-2-imidazoline{{Cite journal |last1=Huang |first1=Xue-Feng |last2=Song |first2=Yu-Mei |last3=Wang |first3=Xi-Sen |last4=Pang |first4=Jie |last5=Zuo |first5=Jing-Lin |last6=Xiong |first6=Ren-Gen |date=2006-02-15 |title=Crystal structures of amarine and isoamarine and copper(I) coordination chemistry with their allylation products |url=https://www.sciencedirect.com/science/article/abs/pii/S0022328X05008788 |journal=Journal of Organometallic Chemistry |volume=691 |issue=5 |pages=1065–1074 |doi=10.1016/j.jorganchem.2005.10.040 |issn=0022-328X|url-access=subscription }}) were discovered early in the history of organic chemistry (between 1841 and 1847),{{Cite journal |last1=Japp |first1=Francis R. |last2=Robinson |first2=H. H. |date=1882-01-01 |title=L.—On the constitution of amarine and lophine |url=https://pubs.rsc.org/en/content/articlelanding/1882/ct/ct8824100323 |journal=Journal of the Chemical Society, Transactions |language=en |volume=41 |pages=323–329 |doi=10.1039/CT8824100323 |issn=0368-1645}} before the development of a structural theory of organic chemistry by Kekulé and Couper in the 1850s. Lophine is prepared by condensation of benzaldehyde, benzil, and ammonia.{{cite journal |doi=10.1002/jhet.4771 |title=Catalyst-free one-pot synthesis of 2,4,5-tri- and 1,2,4,5-tetrasubstituted imidazoles |date=2024 |last1=Bandivadekar |first1=Priyanka V. |last2=Chaturbhuj |first2=Ganesh U. |journal=Journal of Heterocyclic Chemistry |volume=61 |issue=3 |pages=430–438 }}