Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Ngan, Tung-Wan; Ko, Chi‐Chiu; Zhu, Nianyong; Yam, Vivian Wing‐Wah

doi:10.1021/ic061359c

Cited by 78 publications

(22 citation statements)

References 38 publications

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“…The photochromism of these ligands has also been shown to be sensitized by the 3 MLCT excited state of different metal complex systems including the bis(alkynyl)platinum(II) [37] and tris(bipyridyl)ruthenium(II) complexes (Figure 2.14d) [38]. However, it could not be sensitized by the 3 LL ′ CT excited state of the bis(thiolate)zinc(II) complexes [39]. Subsequently, similar design of the diarylethene-containing diimine (L8-L9) and pyridyl N-heterocyclic carbene (L10-L12) ligands based on the 2-pyridylimidazoles has also been reported [40,41].…”

Section: Photosensitization Of Diarylethene-containing Ligandsmentioning

confidence: 99%

Photochromic Transitional Metal Complexes for Photosensitization

Yam

2016

Photochromic Materials: Preparation, Properties and Applications

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IntroductionPhotochemical reactions of most organic compounds (except those with carbonyl substituent) occur predominantly at the lowest-lying singlet excited state (S 1 ). This is attributed to the very inefficient intersystem crossing (ISC) from the singlet to the triplet state due to its spin-forbidden nature. In contrast, triplet excited-state photochemistry of carbonyl-containing organic compounds are well reported because the singlet-triplet energy splitting of these types of compounds are much smaller, leading to the effective population of their triplet excited state on light absorption [1]. To tackle the inefficient ISC, the photoreactivity of an organic compound derived from the triplet state can be achieved by using a triplet photosensitizer, through which light is absorbed by the photosensitizer and energy is transferred from its triplet excited state to the acceptor organic molecule to populate the triplet excited state (Figure 2.1). To achieve photosensitization, which bypasses the reactivity from singlet excited states, the photosensitizer must possess long-lived and higher-lying triplet (T 1 ) energy than the acceptor organic molecule for efficient energy transfer but lower-lying singlet state (S 1 ) for selective photoexcitation of the photosensitizer (Figure 2.1).In the organic photochromic systems, even though the photochromism is originated from different reaction mechanisms such as reversible trans-cis photoisomerizations as well as the reversible photoinduced ring-opening and ring-closing reactions, most of these reactions are derived from the excited singlet state [2]. Studies on the photochromic reactivity of azo compounds [3], stilbenes [3], spiropyrans [4], and spirooxazines [5] via the triplet excited-state pathway achieved by intermolecular photosensitization with organic photosensitizers have also been reported in the literature [3][4][5]. Along with the rapid development of phosphorescent metal polypyridine complexes in the 1970s, diffusion-controlled intermolecular sensitization of photochromic reactions of stilbenes with the triplet excited state of tris(bipyridyl)ruthenium(II) [6] and tricarbonyl rhenium(I) bipyridine [8] complexes has been demonstrated. The

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Section: Photosensitization Of Diarylethene-containing Ligandsmentioning

confidence: 99%

Photochromic Transitional Metal Complexes for Photosensitization

Yam

2016

Photochromic Materials: Preparation, Properties and Applications

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“…As the emissions of the two materials are very similar to the free H3BTC ligand located at 370 nm and Phen at ca 390 nm (Fang et al, 2006;Fu et al, 2002), they may be ligand-centred electronic transitions perturbed by the coordination to metal ions rather than to protons. Meanwhile, these two Zn-MOFs show clearly the effect of the framework density and coordination environment of Zn clusters, which lead to the difference in their photoluminescence behaviour (Ngan et al, 2007;Chen et al, 2003).…”

Section: Crystal Propertiesmentioning

confidence: 99%

Two novel Zn-MOFs: structures and characterization

Ran

Han²,

Pan

et al. 2012

Acta Crystallogr Sect B

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Two novel three-dimensional Zn-MOFs (zinc metal-organic frameworks), Zn(5)(μ(3)-OH)(BTC)(3)(Phen)(4)·5H(2)O (denoted as HUT-11) and Zn(4)(μ(4)-O)(BTC)(2)(Phen)(2)·4H(2)O (denoted as HUT-12), have been synthesized by metal-ligand-directed assembly under hydrothermal conditions. Here, BTC and Phen are denoted as 1,3,5-benzenetricarboxylate and phenanthroline. HUT-11 contains two kinds of secondary building units (SBUs), Zn(3)(μ(3)-OH)(COO)(5) clusters and Zn(2)(COO)(4) clusters. This material exhibits a new three-dimensional (3,4,5)-connected topology with the Schläfli symbol (4·6·8)(2)(4·8(2))(4·6(4)·8(5))(4(2)·6(2)·8(2)). Two perpendicular planes cross at five coordinated Zn1-Zn3-Zn5 nodes, giving a new three-dimensional network. HUT-12 is composed of Zn(4)(μ(4)-O)(COO)(6) clusters as the secondary building units and displays a two-dimensional (3,6)-connected TiS(2) related net topology with the Schläfli symbol (4(2)·6)(4(4)·6(2)·8(8)·10). Both MOFs show blue light emission and a high thermal stability above 673 K.

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“…Our group has recently directed our interests in functionalizing materials with diarylethenes and studying their photochromic behavior. [6] With our recent experience in working on photochromic fused-thiophene systems, [6f] we have ex-tended our interest towards the functionalization of dithieno[3,2-b:2',3'-d]pyrroles owing to their desirable semiconducting properties and their ease of functionalization at the pyrrole ring. Introduction of an optically addressable switching unit into dithieno[3,2-b:2',3'-d]pyrrole system may give rise to new classes of interesting materials with photoswitchable luminescence and electronic properties.…”

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confidence: 99%

“…Upon excitation at the transition band at 360 nm in degassed benzene, the solutions of compound 1-5 showed photochromic behavior, turning from colorless to reddish purple, with the growth of an intense absorption band at approximately 370 nm and a broad absorption at about 558 nm in the UV/ Vis spectra ( Figure 2), typical of the absorptions of the closed form. [5,6] Two well-defined isosbestic points at about 290 and 352 nm were observed, suggesting the photocyclization of only a pair of diarylethene units, probably due to the effective energy transfer from the dithienylethene moiety to the 8a,8b-dimethyl-1,8-dithia-as-indacene moiety (closed form) after the first cyclization, [6f, 8] as illustrated in Scheme 2. Further prolongation of irradiation did not produce the double photocyclized product.…”

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Design and Synthesis of a New Class of Photochromic Diarylethene‐Containing Dithieno[3,2‐b:2′,3′‐d]pyrroles and Their Switchable Luminescence Properties

Wong

Lam

et al. 2009

Chemistry A European J

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Conjugated acenes and heteroacenes have received enormous attention in the past decade or so owing to their probable applications in the fabrication of high-performance semiconductor devices.[1] Amongst them, dithieno[3,2-b:2',3'-d]pyrroles represent one class of interesting compounds that can function as efficient fluorescent materials, [2] low-bandgap field-effect transistors, and organic semiconductors.[3] In addition, the recent interest in the development of nondoped organic light-emitting diodes (OLEDs), which often requires bipolar design to facilitate exciton formation, [4a-e] has led to the exploration of common electron donors such as triarylamine and carbazole. [4f-m] Being an analogue of carbazole, dithienopyrrole derivatives have also been explored for use as a new class of bipolar materials in high efficiency OLEDs.[4n]On the other hand, photochromic diarylethenes also possess excellent and promising switching properties, [5] with high fatigue resistance, high stability, and fast response time. Our group has recently directed our interests in functionalizing materials with diarylethenes and studying their photochromic behavior.[6] With our recent experience in working on photochromic fused-thiophene systems, [6f] we have ex- Of the different methods employed in synthesizing the dithieno[3,2-b:2',3'-d]pyrrole core, [7] the synthetic methodology developed by Rasmussen and co-workers [7a,e] was adopted. Tetrabromination of dithieno[3,2-b:2',3'-d]pyrrole followed by subsequent Suzuki cross-coupling reaction in the presence of an excess of 2,5-dimethylthien-3-yl boronic acid, aqueous Na 2 CO 3 and a catalytic amount of [PdA

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Syntheses, Luminescence Switching, and Electrochemical Studies of Photochromic Dithienyl-1,10-phenanthroline Zinc(II) Bis(thiolate) Complexes

Cited by 78 publications

References 38 publications

Photochromic Transitional Metal Complexes for Photosensitization

Photochromic Transitional Metal Complexes for Photosensitization

Two novel Zn-MOFs: structures and characterization

Design and Synthesis of a New Class of Photochromic Diarylethene‐Containing Dithieno[3,2‐b:2′,3′‐d]pyrroles and Their Switchable Luminescence Properties

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