N,Nʹ-diarylformamidines: Solid state structural analysis and steric-induced stereochemical exchange in solution

Pastor, Michael B.; Feng, Chao; Tsai, Y.C.; Watson, Amelia; Zhao, Qinxin

doi:10.1016/j.tet.2021.131995

Cited by 3 publications

(5 citation statements)

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“…Therefore, complex Au1 shows 0.03 Å longer donoracceptor C1(CAAC)•••N2(Amide) separation compared with Au2 or CMA1. Complex Au1 crystallizes with the formamidinatedonor having a rare cis-conformation [36,37] where the C═N moiety points opposite to the amido N─Au bond (Figure 1c), thus providing efficient electron delocalization due to the 𝜋-extended and conjugated nature of the formamidinato ligand. Recently, we reported that analogous formamidine and guanidine complexes with (CAAC)Cu(I)-moiety adopt the most common transconformation in the solid state while experiencing dynamic cis/trans-isomerization in solution (Figure 1c,d).…”

Section: Resultsmentioning

confidence: 99%

“…C─N bond rotation in the formamidine ligand for solutions of the linear gold complex Au1 (c). [36,37] Molecular structure for the analogous copper formamidine CMA complex having a Y-shape geometry around the copper atom (d). [38] 𝜋-extended benzoguanidine-amide donor ligand with a mirrorplane passing through the C 25 ─N 4 bond, thus resulting in the exclusive formation of the trans-isomer.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Molecular and crystal structures of carbene metal amides Au1 (a) and Au2 (b).Ellipsoids are shown at 50% probability. C─N bond rotation in the formamidine ligand for solutions of the linear gold complex Au1 (c) [36,37]. Molecular structure for the analogous copper formamidine CMA complex having a Y-shape geometry around the copper atom (d) [38].…”

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confidence: 99%

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Deep‐Blue and Fast Delayed Fluorescence from Carbene–Metal–Amides for Highly Efficient and Stable Organic Light‐Emitting Diodes

Brannan,

Cho,

Reponen

et al. 2024

Advanced Materials

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Linear gold complexes of the “carbene‐metal‐amide” (CMA) type are prepared with a rigid benzoguanidine amide donor and various carbene ligands. These complexes emit in the deep‐blue range at 424 and 466 nm with 100% quantum yields in all media. The deep‐blue thermally activated delayed fluorescence (TADF) originates from a charge transfer state (CT) with an excited state lifetime as low as 213 ns, resulting in fast radiative rates of 4.7 × 106 s−1. The high thermal and photo‐stability of these CMA materials enabled us to fabricate highly energy efficient organic light‐emitting diodes (OLED) in host‐guest architectures. We report deep‐blue OLED devices with electroluminescence at 416 nm and 457 nm with practical external quantum efficiencies of up to 23% at 100 cd m−2 with excellent colour coordinates CIE (x; y) = 0.16; 0.07 and 0.17; 0.18. The operating stability of these OLEDs is the longest reported to date (LT50 = 1 hour) for deep‐blue CMA emitters, indicating a high promise for further development of blue OLED devices. Our findings inform the molecular design strategy and correlation between delayed luminescence with high radiative rates and CMA OLED device operating stability.This article is protected by copyright. All rights reserved

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Deep‐Blue and Fast Delayed Fluorescence from Carbene–Metal–Amides for Highly Efficient and Stable Organic Light‐Emitting Diodes

Brannan,

Cho,

Reponen

et al. 2024

Advanced Materials

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“…[ 25 ] Another interesting feature of formamidines is their capability to form different isomers and tautomers depending on the position of the substituents, which consequently influence bonding. [ 26 ]…”

Section: Introductionmentioning

confidence: 99%

Silver(I) complexes ofN,N′‐diarylformamidine ligands: Synthesis, crystal structures, and in vitro antibacterial studies

Bongoza

Zamisa

Munzeiwa

et al. 2022

Applied Organom Chemis

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Nine silver(I) N,N′‐diarylformamidine complexes of type [Ag (Ln)2X] (where X = NO3−, CF3COO−, and CF3SO3−, n = 1–5) were synthesised and characterised by physiochemical and spectroscopic techniques. Further confirmation for the formation of the complexes was provided by single‐crystal X‐ray crystallography. All complexes (but one) adopted linear geometry in which coordination was via two N atoms of two formamidine ligands with the anion (X) displaced from coordination sphere. In the structure of the exception, the anion is part of the coordination sphere and a T‐shaped geometry was adopted. The antimicrobial activity of the Ag(I) complexes were investigated against two Gram‐positive bacteria, that is, S. aureus ATCC 25923 and Methicillin‐resistant S. aureus ATCC 700699 (MRSA) and four Gram‐negative bacteria, that is, K. pneumoniae ATCC 31488, S. typhimurium ATCC 14026, P. aeruginosa ATCC 27853 and E. coli ATCC 25922 and they were evaluated based on ciprofloxacin and silver nitrate standards. The newly synthesised target complexes demonstrated promising antibacterial activity against Gram‐positive bacteria although less than the reference drug ciprofloxacin. The best active silver(I) complex contains a nitrate counter‐ion.

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Synthesis, Characterisation, and Coordination Behaviour of Novel Pyridyl‐formamidine Based Mn(I), Cu(II), Zn(II), and Pd(II) Complexes

Mana Edor,

Cassiem Joseph,

Jordaan

et al. 2024

Eur J Inorg Chem

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We report a new synthetic approach for the synthesis of less‐explored unsymmetrical pyridyl‐formamidine ligands and their coordination behaviour to form Mn(I), Cu(II), Zn(II), and Pd(II) complexes. The one‐step process for synthesising the unsymmetrical pyridyl‐formamidine compounds offers the advantage of being functional‐group tolerant and less cumbersome. Generally, the pyridyl‐formamidine ligands coordinate to the metal centres in a bidentate fashion to form a six‐membered chelate as established by spectroscopic and crystallographic analysis. It was observed that the formamidine functionality is prone to hydrolysis in the presence of methoxy substituent on the phenyl ring and/or acetate‐containing metal precursors.

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N,Nʹ-diarylformamidines: Solid state structural analysis and steric-induced stereochemical exchange in solution

Cited by 3 publications

References 59 publications

Deep‐Blue and Fast Delayed Fluorescence from Carbene–Metal–Amides for Highly Efficient and Stable Organic Light‐Emitting Diodes

Deep‐Blue and Fast Delayed Fluorescence from Carbene–Metal–Amides for Highly Efficient and Stable Organic Light‐Emitting Diodes

Silver(I) complexes ofN,N′‐diarylformamidine ligands: Synthesis, crystal structures, and in vitro antibacterial studies

Synthesis, Characterisation, and Coordination Behaviour of Novel Pyridyl‐formamidine Based Mn(I), Cu(II), Zn(II), and Pd(II) Complexes

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