Triptycene<sup>1</sup> (9,10-o-Benzenoanthracene)

Bartlett, Paul D.; Ryan, MP; Cohen, Saul G.

doi:10.1021/ja01263a035

Cited by 263 publications

(216 citation statements)

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“…[5] Triptycene was first reported by Bartlett and co-workers in 1942, but its synthesis suffered from lengthy procedures and harsh conditions. [6] In 1956, Wittig and Ludwig reported a simple synthesis of triptycene in one step from benzyne and anthracene, which was eventually adopted to make the synthesis of triptycene a standard undergraduate laboratory "experiment". [7] After that, interest in triptycene and its derivatives increased gradually, owing to their special structure, as well as electrochemical and photochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Zhang

Liu

et al. 2014

Chemistry An Asian Journal

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In the past decades, the naphthalimide structure has found application in many areas of chemistry due to its unique photophysical properties. Naphthalimide has two isomers, 1,8-naphthalimide containing a six-membered imide ring and 2,3-naphthalimide containing a five-membered imide ring. The former has been widely investigated while studies on the latter are considerably more rare. On the other hand, naphthalimide can also be regarded as a building block to construct polycyclic aromatic hydrocarbons (PAHs), which have found wide applications in optical materials. Here we report the synthesis and optoelectronic properties of three 2,3-naphthalimide-based triptycenes. These three triptycene derivatives enrich the family of triptycenes.

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Section: Introductionmentioning

confidence: 99%

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Zhang

Liu

et al. 2014

Chemistry An Asian Journal

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“…King and co-workers 38 improved the earlier reported method by Skvarchenko and co-workers 39 for the bromination of triptycene (1). Consequently, triptycene (1) was dissolved in chloroform and stirred in the presence of iron filings at 25 °C.…”

Section: Scheme 24 Fluorination Of Triptycene (1)mentioning

confidence: 92%

“…Scheme 10 Synthesis of β-substituted triptycenes Scheme 11 Selective formylations of triptycene (1) In 2012, when we attempted the selective synthesis of formyltriptycene, we found that this aluminum chloride catalyzed Friedel-Crafts acylation of triptycene did not stop at the mono-or di-formylated stage. 25 Further studies showed that treatment of triptycene (1) with 1.5 equivalents of dichloro(methoxy)methane and 1.2 equivalents of stannic chloride (SnCl 4 ) in dichloromethane at 0 °C, for one hour, gave selectively 2-formyltriptycene (23) in 60% yield (Scheme 11a).…”

Section: Account Syn Lettmentioning

confidence: 99%

“…Later, Zupan and Šket 37 made use of xenon difluoride (XeF 2 ) in the presence of hydrogen fluoride (HF) to achieve the selective fluorination of triptycene (1). As shown in Scheme 24, treatment of triptycene (1) with one equivalent of xenon difluoride, in dichloromethane at room temperature in the presence of a catalytic amount of hydrogen fluoride, provided two fluorination products, 2-fluorotriptycene (79) and 1-fluorotriptycene (80).…”

Section: Scheme 23 Perchlorination Of Triptycene (1)mentioning

confidence: 99%

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Synthesis of Substituted Iptycenes

Meng

Chen

2014

Synlett

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Iptycenes are a class of aromatic compounds that contain several arene units fused to a bicyclo[2.2.2]octatriene bridgehead system. This unique, rigid, three-dimensional molecular structure provides several open electron-rich cavities with an abundance of reactive positions, and makes them useful for a wide range of applications. There is no doubt that the synthesis and reactions of iptycene derivatives with different functional groups form the fundamental basis of iptycene development. In this account, the synthesis of substituted iptycenes is described. In particular, the different synthetic strategies toward substituted triptycenes and pentiptycenes are the main focus. 1 Introduction 2 Synthesis of Substituted Triptycenes 2.

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“…Since the first synthesis of triptycene (1) by Bartlett and co-workers in 1942 (Ref. 6), transannular electronic interaction between the remote (nonconjugated) benzene rings has been of particular interest and still remains a matter of controversy (Ref. 7).…”

Section: Introductionmentioning

confidence: 99%

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

Murata¹

1983

Pure and Applied Chemistry

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-The group theoretical analysis of the electronic structure of l,4-dihydro-l,4-bis (dicyanoinethylene)triptycene leads to an interesting but rarely documented notion, "charge transfer transition for symmetry forbidden charge transfer interaction" , which was supported by the substituent effects on the charge transfer band shifts. The substituent effects on the charge transfer band shifts were also observed in a series of 9,lO-dihydro-9, l0-o-benzenoanthracene-l,4-diones. These results provide decisive evidence for the fact that the orbitals involved in the ground state charge transfer interaction need not be the same as those involved in the charge transfer transition. In general, charge transfer phenomena between donor and acceptor components fixed in the rigid frameworks of C2v and C5 point groups are also discussed by means of the symmetry properties of the interacting orbitals.

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Triptycene¹ (9,10-o-Benzenoanthracene)

Cited by 263 publications

References 0 publications

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Synthesis of Substituted Iptycenes

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

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Triptycene1 (9,10-o-Benzenoanthracene)

Cited by 263 publications

References 0 publications

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Naphthalimide‐Based Triptycenes: Synthesis and Optoelectronic Properties

Synthesis of Substituted Iptycenes

Charge transfer transition for symmetry-forbidden charge transfer interaction. Theory and experimental verification

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Product

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About

Triptycene¹ (9,10-o-Benzenoanthracene)