[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

Kahl, Paul; Wagner, J. Philipp; Balestrieri, Ciro; Becker, Jonathan; Hausmann, Heike; Bodwell, Graham J.; Schreiner, Peter R.

doi:10.1002/anie.201602201

Cited by 29 publications

(13 citation statements)

References 55 publications

(27 reference statements)

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“…[18,53] The role of the spacer is highlighted, particularly,t hrough ac omparison of dimers 23 and 41,w here the non-conjugated spaceri so fs imilar length (four and three sp 3 -hybridized carbons, respectively), Figure 4. Comparison of spacers derived a) from meta-diethynylbenzene, and b) 1,3-diethynyladamantane,a nd c) X-ray crystallographic analyses of the two moieties (red, ccdc = OVACEV [84] and blue, ccdc = HEFKEJ, [85] respectively).…”

Section: 6'-linked Pentacene Dimersmentioning

confidence: 99%

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Pentacene Dimers as a Critical Tool for the Investigation of Intramolecular Singlet Fission

Hetzer

Guldi

Tykwinski

2018

Chemistry A European J

132

176

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Singlet fission (SF) involves the spontaneous splitting of a photoexcited singlet state into a pair of triplets, and it holds great promise toward the realization of more efficient solar cells. Although the process of SF has been known since the 1960s, debate regarding the underlying mechanism continues to this day, especially for molecular materials. A number of different chromophores have been synthesized and studied in order to better understand the process of SF. These previous reports have established that pentacene and its derivatives are especially well-suited for the study of SF, since the energetic requirement E(S )≥2E(T ) is fulfilled rendering the process exothermic and unidirectional. Dimeric pentacene derivatives, in which individual pentacene chromophores are tethered by a "spacer", have emerged as the system of choice toward exploring the mechanism of intramolecular singlet fission (iSF). The dimeric structure, and in particular the spacer, allows for controlling and tuning the distance, geometric relationship, and electronic coupling between the two pentacene moieties. This Minireview describes recent advances using pentacene dimers for the investigation of iSF.

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Section: 6'-linked Pentacene Dimersmentioning

confidence: 99%

“… Comparison of spacers derived a) from meta ‐diethynylbenzene, and b) 1,3‐diethynyladamantane, and c) X‐ray crystallographic analyses of the two moieties (red, ccdc=OVACEV and blue, ccdc=HEFKEJ, respectively).…”

Section: 6′‐linked Pentacene Dimersmentioning

confidence: 99%

Pentacene Dimers as a Critical Tool for the Investigation of Intramolecular Singlet Fission

Hetzer

Guldi

Tykwinski

2018

Chemistry A European J

132

176

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“…The observation that the best result was observed in the solvent with the highest dielectric constant ( ϵ =36.6) suggests that there is developing charge at the transition state of the reaction. It has been noted previously that some (2,7)pyrenophanes have relatively large calculated dipole moments that increase with the degree of bend in the pyrene system ( μ =0.87–1.74 D) [27] and an adamantano(2,7)pyrenophane was calculated to have a dipole moment 2.3 D [28] . Therefore, the dipole moments of 5 a ‐ d were calculated at the B3LYP‐D3/6‐31G(d) level of theory and found to be almost identical ( μ =2.31–2.39 D), despite the range of bend in the teropyrene system (Supporting Information, Sec.…”

Section: Resultsmentioning

confidence: 87%

Gram‐Scale Synthesis of the 1,1,n,n‐Tetramethyl[n](2,11)teropyrenophanes

Unikela

Ghasemabadi

Houska

et al. 2020

Chemistry A European J

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Ag ram-scale synthesis of as eries of 1,1,n,n-tetramethyl[n](2,11)teropyrenophanes (n = 7-9) has been accomplished as well as the first synthesis of the next higher homologue 1,1,10,10-tetramethyl[10](2,11)teropyrenophane. The scale-up of the original small-scale synthesis required the development of several heavily modified synthetic methods, including ac hlorination/Friedel-Crafts alkylation protocol and an iodination/Wurtz coupling protocol, which were performed on 25-30 ga nd 30-60g scales, respectively.T wo separate sets of conditions for the key teropyrene-forming cyclodehydrogenation reaction at the end of the synthetic pathway were developed,a na cid-promoted one for the two less strained congeners anda na cid-free method for the two more strained homologues.

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“…Subsequent bromination and cyclization afforded the pyrene-substituted adamantane. 117 Interestingly, this hybrid structure exhibits a large dipole moment due to orthogonal arrangement of the 1,3-disubstituted adamantane and pyrene moiety. Introduction of three substituents at the 1,3,5-positions of adamantane adopts a tripodal geometry.…”

Section: 3-disubstituted Adamantanesmentioning

confidence: 99%

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

Grover

Senge²

2020

Synthesis

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The remarkable structural and electronic properties of rigid non-conjugated hydrocarbons afford attractive opportunities to design molecular building blocks for both medicinal and material applications. The bridgehead positions provide the possibility to append diverse functional groups at specific angles and in specific orientations. The current review summarizes the synthetic development in CH functionalization of three rigid scaffolds namely: (a) cubane, (b) bicyclo[1.1.1]pentane (BCP), (c) adamantane.1 Introduction2 Cubane2.1 Cubane Synthesis2.2 Cubane Functionalization3 Bicyclo[1.1.1]pentane (BCP)3.1 BCP Synthesis3.2 BCP Functionalization4 Adamantane4.1 Adamantane Synthesis4.2 Adamantane Functionalization5 Conclusions and Outlook

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[2](1,3)Adamantano[2](2,7)pyrenophane: A Hydrocarbon with a Large Dipole Moment

Cited by 29 publications

References 55 publications

Pentacene Dimers as a Critical Tool for the Investigation of Intramolecular Singlet Fission

Pentacene Dimers as a Critical Tool for the Investigation of Intramolecular Singlet Fission

Gram‐Scale Synthesis of the 1,1,n,n‐Tetramethyl[n](2,11)teropyrenophanes

Synthetic Advances in the C–H Activation of Rigid Scaffold Molecules

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