[2.2]Paracyclophane-based molecular systems for the development of organic solar cells

Valentini, Luca; Marrocchi, Assunta; Seri, Mirko; Mengoni, F.; Meloni, Fabio; Taticchi, A.; Kenny, J. M.

doi:10.1016/j.tsf.2007.12.075

Cited by 28 publications

(15 citation statements)

References 21 publications

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“…Besides, OSMs will receive high V OC which were benefited from the deep-lying HOMO level caused by the electron-withdrawing effect of alkyne. Hence, alkyne including acetylene and arylacetylenes is a promising class of π-bridge [78][79][80][81][82][83]. Fig.…”

Section: π-Linkage With Alkynementioning

confidence: 99%

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Yin

2016

Sci. China Mater.

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Much attention has been paid to the push-pullstructure organic small molecule (OSM) materials for photovoltaic (PV) application in the past decade, due to their facile reduction of energy band gap (Eg) and effective control of PV properties. π-bridge plays an important role in the push-pull-structure OSMs since an appropriate π-linkage is crucial for improving the PV performance of organic solar cells (OSCs). In this review, various π-bridge groups (thiophene, alkene, alkyne, arene and heterocycle) and the pertinent π-linkage effect will be systematically summarized. These results suggest that the in-depth study of the π-linkage effect is essential to deeply understanding the relationship between the molecular structure and property, thus improving PV performance.

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Section: π-Linkage With Alkynementioning

confidence: 99%

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Yin

2016

Sci. China Mater.

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“…On the other hand , direct steric interaction with alkynes may result in a bending distortion, but conjugation will be maintained due to the cylindrical electronic symmetry of the triple bond. [28] Quite recently, some of us have reported [29][30][31][32][33][34][35][36] a new family of monosubstituted acetylenic [2.2]paracyclophanes, exploiting the possibility of constructing three-dimensional p-systems that show the usual overlap of p-orbitals in benzene rings, as well as the cofacial electronic overlap between the decks of a paracyclophane. Studies on the impact of the conjugation length and/or the presence of different (hetero)aromatic nuclei on the electronic communication were accomplished.…”

Section: Acetylenic [22]paracyclophanesmentioning

confidence: 99%

Organic Small Molecules for Photonics and Electronics from the [2.2]Paracyclophane Scaffold

Marrocchi

Tomasi

Vaccaro

2012

Israel Journal of Chemistry

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In the search for molecules for organic photonics and electronics, several strategies have been used to modulate physical and chemical properties of [2.2]paracyclophane derivatives by sequential functionalization of their three‐dimensional cores. This review summarizes the major design and synthetic strategies for tuning paracyclophane‐containing small molecules by introducing various moieties featuring (hetero)aromatic rings directly connected to each other, as well as alternating (hetero)aryl and ethylene or ethynylene units. Several examples are presented that elucidate the structural, optical, and electronic consequences of incorporating these fragments in the aromatic decks, particularly relating to applications in organic optoelectronics.

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“…This prediction has turned out to be true, as shown by us [3][4][5][6][7] and several other groups. [8][9][10][11][12][13][14] Furthermore, the [2. 2]paracyclophane core has turned out to be an interesting and useful spacer molecule.…”

Section: Introductionmentioning

confidence: 99%

Preparation, Structural Properties and Thermal Isomerization of Hex‐3‐ene‐1,5‐diyne Bridged [2.2]Paracyclophanes

Dix

Bondarenko

Jones

et al. 2014

Chemistry A European J

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The [2.2]paracyclophane moiety is used as a spacer to connect the ends of a hex-3-ene-1,5-diyne unit, a π-system that on thermolysis usually cycloaromatizes to a benzene ring (Bergman cyclization). For the preparation of the pseudo-geminally-bridged system 9, the diacetylene 3 was chain-extended to the diol 16, which after conversion to the pseudo-geminal dibromide 17 was ring-closed by treatment with LiHMDS/HMPA to the [2.2]paracyclophane enediyne 9. Whereas the McMurry coupling of the pseudo-ortho bisaldehyde 24 resulted in the formation of the hexadienyne-bridged cyclophane 27, the pseudo-ortho-bridged hydrocarbon 11 was obtained by preparing first the diol 28 from 24, converting the latter into the dioxolane 29, which in the last step furnished the olefin 11 by treatment with Tf2 O/EtN(iPr)2 . The authentic Bergman product 10 of the pseudo-gem-bridged hexenediyne 9 was synthesized by a conventional sequence starting from the ethynyl formyl substrate 18. Since the pseudo-ortho-enediyne-bridged hydrocarbon 11 is thermally labile, its benzannelated derivate 34 was prepared. No classical Bergman cyclization reactions could be observed for any of the [2.2]paracyclophane-bridged hexenediynes prepared here. In the pseudo-gem-series the fulvenes 14 and 15 were the only products that could be identified under thermal conditions (McMurry coupling); the benzannelated substrate 34 gave the benzofulvene-bridged cyclophane 36 on photolysis. Bergman cyclizations yielding fulvene derivatives are extremely rare. The mechanism of the cyclization of 9 and 34 is discussed, using compliance constants. The structure assignments of the hydrocarbons synthesized in this study are based on spectroscopic studies as well as X-ray structural analyses for 9, 10, 11, 27, and 34.

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[2.2]Paracyclophane-based molecular systems for the development of organic solar cells

Cited by 28 publications

References 21 publications

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

π-Linkage effect of push-pull-structure organic small molecules for photovoltaic application

Organic Small Molecules for Photonics and Electronics from the [2.2]Paracyclophane Scaffold

Preparation, Structural Properties and Thermal Isomerization of Hex‐3‐ene‐1,5‐diyne Bridged [2.2]Paracyclophanes

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