Gold(I) Styrylbenzene, Distyrylbenzene, and Distyrylnaphthalene Complexes: High Emission Quantum Yields at Room Temperature

Abstract

One gold(I)-substituted styrylbenzene, six digold(I) distyrylbenzenes, one tetragold distyrylbenzene, and four digold distyrylnaphthalene complexes were synthesized using base-promoted auration, alkynylation, triazolate formation, and Horner-Wadsworth-Emmons reactions. The gold(I) fragments are either σ-bonded to the aromatic system, or they are attached through an alkynyl or triazolate spacer. Product formation was monitored using (31)P{(1)H} NMR spectroscopy. Systems in which gold(I) binds to the central benzene ring or the terminal phenyl rings were designed. All of these complexes have strong ultraviolet absorptions and emit blue light. The position of the gold(I) attachment influences the luminescence efficiency. Complexes with two gold(I) fragments attached to the ends of the conjugated system have fluorescence quantum yields up to 0.94, when using 7-diethylamino-4-methylcoumarin as the emission standard. Density-functional theory calculations on three high-yielding emitters suggest that luminescence originates from the distyrylbenzene or -naphthalene bridge.

Enhancement of the Luminescent Efficiency in Carbene-Au(I)-Aryl Complexes by the Restriction of Renner–Teller Distortion and Bond Rotation

“…Yield: 44 mg (83%). 1 H NMR (400 MHz, acetone): δ 7.54 (t, J = 7.8 Hz, 2H, p-ArH (dipp)), 7.39 (d,J = 7.8 Hz,4H,2H,6.65 (ddt,J = 8.0,6.8,1.5 Hz,1H,2H,, 3.04 (sept, J = 6.7 Hz, 4H, CH(CH 3 ) 2 ), 1.87 (s, 6H, C(CH 3 ) 2 ), 1.39 (d, J = 6.8 Hz, 12H, CH(CH 3 ) 2 ), 1.19 (d, J = 6.8 Hz, 12H, CH(CH 3 ) 2 ). 13 (DAC)Au (I) (4-carbazolylphenyl) (1b (DAC)Au (I) (4-diphenylaminophenyl) (1c).…”

Deactivation Routes in Gold(I) Polypyridyl Complexes: Internal Conversion Vs Fast Intersystem Crossing

“…The design of compounds exhibiting high triplet yields continues to attract much interest mainly because of their potential − in many different fields. In particular, gold­(I) complexes, because of the unique properties of gold, show potential uses as advanced materials, therapeutic drugs, photodynamic therapy agents, and sensors, among others. − …”

Cyclometalated (boroxinato)gold(iii) complexes from arrested transmetalation

“…We and others have applied boron transmetalation to the synthesis of (phosphine)-and (N-heterocyclic carbene)gold(I) aryls. [16][17][18][19][20][21][22][23][24][25][26] Reaction conditions can be selected to yield mono-gold(I) species or geminally diaurated aryls. 30,31 Analogous transmetalation reactions, mediated by boron, afford cyclometalated iridium(III) in roomtemperature reactions.…”