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Acridine N ‐Heterocyclic Carbene Gold(I) Compounds: Tuning from Yellow to Blue Luminescence
Author(s) -
Vaddamanu Moulali,
Sathyanarayana Arruri,
Masaya Yamane,
Sugiyama Shohei,
Kazuhisa Ozaki,
Velappan Kavitha,
Nandeshwar Muneshwar,
Hisano Kyohei,
Tsutsumi Osamu,
Prabusankar Ganesan
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202001380
Subject(s) - alkyl , carbene , chemistry , luminescence , imidazole , chloride , ligand (biochemistry) , medicinal chemistry , molecule , photochemistry , crystallography , stereochemistry , organic chemistry , materials science , catalysis , receptor , optoelectronics , biochemistry
The synthesis and the luminescence features of three gold(I)‐ N ‐heterocyclic carbene (NHC) complexes are presented to study how the n ‐alkyl group can influence the luminescence properties in the crystalline state. The mononuclear gold(I)‐NHC complexes, [( L 1 )Au(Cl)] ( 1 ), [( L 2 )Au(Cl)] ( 2 ), and [( L 3 )Au(Cl)] ( 3 ) were isolated from the reactions between [(tht)AuCl] and corresponding NHC ligand precursors, [ N ‐(9‐acridinyl)‐ N’ ‐( n ‐butyl)‐imidazolium chloride, ( L 1 .HCl)], [ N ‐(9‐acridinyl)‐ N’ ‐( n ‐pentyl)‐imidazolium chloride, ( L 2 .HCl)] and [ N ‐(9‐acridinyl)‐ N’ ‐( n ‐hexyl)‐imidazolium chloride, ( L 3 .HCl)]. Their single‐crystal X‐ray analysis reveals the influence of the n ‐alkyl groups on solid‐state packing. A comparison of the luminescence features of 1 – 3 with n ‐alkyl substituents is explored. The molecules 1 – 3 depicted blue emission in the solution state, while the yellow emission (for 1 ), greenish‐yellow emission (for 2 ), and blue emission (for 3 ) in the crystalline phase. This paradigm emission shift arises from n ‐butyl to n ‐pentyl and n ‐hexyl in the crystalline state due to the carbon‐carbon rotation of the n‐ alkyl group, which tends to promote unusual solid packing. Hence n ‐alkyl group adds a novel emission property in the crystalline state. Density Functional Theory and Time‐Dependent Density Functional Theory calculations were carried out for monomeric complex, N ‐(9‐acridinyl)‐ N’ ‐( n ‐heptyl)imidazole‐2‐ylidene gold(I) chloride and dimeric complex, N ‐(9‐acridinyl)‐ N’ ‐( n ‐heptyl)imidazole‐2‐ylidene gold(I) chloride to understand the structural and electronic properties.