Synthesis, Structure, and Photophysical Properties of Dibenzo[<i>de</i>,<i>mn</i>]naphthacenes

Wu, Te‐Ho; Chen, Chia Hua; Hibi, Daijiro; Shimizu, Akihiro; Tobe, Yoshito; Wu, Yao Ting

doi:10.1002/anie.201001929

Cited by 89 publications

(48 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 1960s, two leading research groups in annulene chemistry (Sondheimer and Staab) accidentally found the formation of zethrene during the attempted synthesis of 1,2,3:6,7,8-di(1=,8=-naphth) [10]annulene (6) and tetradehydrodinaphtho [10]annulene (9) (Scheme 2). More specifically, in 1968 Mitchell and Sondheimer found that the solution of compound 6 gradually became red in air.…”

Section: Pioneers Of Zethrene Chemistrymentioning

confidence: 99%

“…In 2009, Umeda's group reported the successful synthesis and isolation of the tetradehydrodinaphtho [10]annulene (9) and its subsequent transannular cyclization triggered by addition of iodine to give the 7,14-diiodozethrene 24 (Scheme 4). 9 Compound 24 can serve as a key intermediate for the synthesis of 7,14-substituted zethrene derivatives via transition metal catalyzed cross coupling reactions.…”

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

“…In 2010, Wu's group discovered that Pd-catalyzed cyclodimerization of 1-iodo-8-ethynylnaphthalene derivative 26 gave the bay-substituted zethrenes 27 in good yields. 10 In parallel to those works, our research group was looking for stable organic near-infrared (NIR) dyes, and we believed that the zethrene diimide was a good candidate with superior properties compared to its perylene diimide counterpart. Inspired by the early work done by Mitchell/Sondheimer and Staab, we expected that the synthesis of zethrene diimide 29 could be done by C-C cross coupling reaction followed by in situ transannular cyclization of the tetradehydrodinaphtho [10] annulene intermediate.…”

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

“…10 In parallel to those works, our research group was looking for stable organic near-infrared (NIR) dyes, and we believed that the zethrene diimide was a good candidate with superior properties compared to its perylene diimide counterpart. Inspired by the early work done by Mitchell/Sondheimer and Staab, we expected that the synthesis of zethrene diimide 29 could be done by C-C cross coupling reaction followed by in situ transannular cyclization of the tetradehydrodinaphtho [10] annulene intermediate. Indeed, in 2010, we reported that Stille coupling between the 1,8-dibromo-naphthalene monoimide 28 and bis(tributylstannyl)acetylene directly gave the target zethrene diimide 29 (ZDI) in 20% yield.…”

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

Modern zethrene chemistry

Pan

2017

Can. J. Chem.

View full text Add to dashboard Cite

This paper gives a brief summary of zethrene chemistry after the pioneering works by Clar, Mitchell, Sondheimer, and Staab et al. In the past a few years, various synthetic methods and stabilizing strategies have been developed, which have made the synthesis of stable, vertically and laterally extended zethrenes practically achievable. One of the most important discoveries for this type of molecule is their open-shell diradical character, which is the origin of their unique optical, electronic, and magnetic properties. The fundamental structure-diradical character-physical property relationships were investigated, and these studies form the basis for the tailored design of more general open-shell singlet diradicaloids with controllable diradical character and physical properties.Key words: zethrene, polycyclic aromatic hydrocarbons, diradicaloid, polyradical.Résumé : Cet article présente un résumé de la chimie du zéthrène fondé sur les premiers travaux exploratoires de Clar, Mitchell, Sondheimer et Staab, ainsi que leurs collaborateurs. Au cours des dernières années, diverses méthodes de synthèse et stratégies de stabilisations ont été mises au point, rendant possible du point de vue pratique la synthèse de zéthrènes stables étendus sur les plans vertical et latéral. L'une des découvertes les plus importantes concernant ce type de molécules consiste en leur caractère de diradical à couches ouvertes, qui est à l'origine de leurs propriétés optiques, électroniques et magnétiques particulières. Nous avons étudié les relations entre la structure fondamentale, le caractère diradicalaire et les propriétés physiques. Ces études forment la base d'une conception généralisée aux diradicaloïdes singulets à couches ouvertes dont le caractère diradicalaire et les propriétés physiques seraient réglables. [Traduit par la Rédaction]

show abstract

Section: Pioneers Of Zethrene Chemistrymentioning

confidence: 99%

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

Section: Renaissance Of Zethrene Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Modern zethrene chemistry

Pan

2017

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…84 The development of a more efficient synthesis and characterization by X-ray analysis were achieved by Wu and Tobe in 2010. 85 From the determined structure, the ground state of zethrene can be best represented by the structural formula described in Figure 24, indicating negligible singlet biradical character. Sharp NMR signals support the closed-shell character.…”

Section: Zethrenesmentioning

confidence: 99%