Corannulene derivatives for organic electronics: From molecular engineering to applications

Chen, Rui; Lu, Ru‐Qiang; Shi, Pengjun; Cao, Xiaoyu

doi:10.1016/j.cclet.2016.06.033

Cited by 50 publications

(21 citation statements)

References 96 publications

(116 reference statements)

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“…Whereas the parent corannulene shows a highly disordered packing structure dominated by C-H$$$p interactions, the introduction of imide, trifluoromethyl, cyano, or other groups at the rim positions tend to form a regular columnar stack based on bowl bowl-in-bowl p-p interactions. [55][56][57] Out-of-plane coordination with central heteroatoms of macrocycles provides another way to make the bowl-shaped structures, e.g., boron subphthalocyanine (subPc), boron subporphyrin, titanylphthalocyanine (TiOPc), or vanadylphthalocyanine (VOPc). Most metal phthalocyanies, such as CuPc (Figure 11), are planar structures in a cofacial herringbone packing while TiOPc and VOPc exhibit a shallow square-pyramid structure with the oxygen atom out of the conjugated plane in a 2D brickwork packing motif.…”

Section: Cylinder-like or Disk-like Moleculesmentioning

confidence: 99%

Crystal Engineering of Organic Optoelectronic Materials

Zhen

Dong

et al. 2019

Chem

205

177

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Crystal engineering can be regarded as the highly ordered and complicated supramolecular synthesis of functional crystalline solids by control of intermolecular interactions. As one of the most important organic solids for crystal engineering, organic optoelectronic materials have received tremendous interest in the past several decades. In this review, we discuss systematically how to design organic optoelectronic materials from the perspective of crystal engineering including molecular structures, intermolecular interactions, packing arrangements, crystal growth, and patterning methods as well as two-component and multi-component molecular materials. We underline the correlations among molecular structures, packing modes, crystal morphologies, and optoelectronic properties. Finally, we address several key points for further exploration in this field.

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Section: Cylinder-like or Disk-like Moleculesmentioning

confidence: 99%

Crystal Engineering of Organic Optoelectronic Materials

Zhen

Dong

et al. 2019

Chem

205

177

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“…The (0 0 2) diffraction peak was slightly shifted toward higher angle with increasing the carbonization temperature, indicating the increase of the graphitization degree. The shrink of the (0 0 2) interplanar spacing was mainly due to the decrease of the heteroatoms doping at higher temperature [13].…”

Section: Resultsmentioning

confidence: 95%

Highly nitrogen and sulfur dual-doped carbon microspheres for supercapacitors

Lei

Guo

et al. 2017

Science Bulletin

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“…In contrast, development of buckybowl‐containing materials with desirable properties is still in its infancy. For instance, during the 50 years since the discovery of the first solution route for corannulene preparation (1966), only around 20 papers include any photophysical studies, despite nearly 1000 publications focused on corannulene. To the best of our knowledge, there are only two reports in the area of corannulene solid‐state photophysics.…”

Section: Methodsmentioning

confidence: 99%

Hierarchical Corannulene‐Based Materials: Energy Transfer and Solid‐State Photophysics

et al. 2017

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Abstract:We report the first example of ad onor-acceptor corannulene-containing hybrid material with rapid ligand-toligand energy transfer (ET). Additionally,weprovide the first time-resolved photoluminescence (PL) data for any corannulene-based compounds in the solid state.C omprehensive analysis of PL data in combination with theoretical calculations of donor-acceptor exciton coupling was employed to estimate ET rate and efficiency in the prepared material. The ligand-to-ligand ET rate calculated using two models is comparable with that observed in fullerene-containing materials,w hich are generally considered for molecular electronics development. Thus,the presented studies not only demonstrate the possibility of merging the intrinsic properties of p-bowls, specifically corannulene derivatives,w ith the versatility of crystalline hybrid scaffolds,b ut could also foreshadowt he engineering of anovel class of hierarchicalcorannulene-based hybrid materials for optoelectronic devices.While the compromise between strain and aromaticity is ap ersistent synthetic challenge, [1][2][3] the bowl shape and electronic properties of corannulene derivatives (buckybowls, Scheme 1) imply an unrevealed potential for molecular electronics development similar to their close famous analogues,fullerenes.The main success of the latter in the field of optoelectronics is associated with very fast energy/electron transfer, which has been demonstrated in numerous photophysical studies. [4][5][6] In contrast, development of buckybowlcontaining materials with desirable properties is still in its infancy. Fori nstance,d uring the 50 years since the discovery of the first solution route for corannulene preparation (1966), [1] only around 20 papers [2, include any photophysical studies,d espite nearly 1000 publications focused on corannulene.T othe best of our knowledge,there are only two reports [8,10] in the area of corannulene solid-state photophysics.F urthermore,n os olid-state time-resolved photoluminescence (PL) data or energy transfer (ET) studies have been reported for any corannulene-containing compounds despite the fact that ET rate and efficiency are crucial fundamental parameters for applications ranging from organic photovoltaics to photocatalysis. [33,34] This gap in material development was the major driving force to initiate the presented study,especially taking into account the recent progress in corannulene chemistry. [35] Our shift from more traditional flat aromatic hydrocarbons [36] towards p-bowls (for example,c orannulene) was also driven by 1) their significant dipole moment, 2) the possibility to extend the dimensionality of 3D hybrid frameworks through the p-bowl curvature,3 )potential for charge stabilization on the surface owing to doubly degenerate lowest unoccupied molecular orbitals (LUMOs), 4) anticipated effective intermolecular charge transport, and 5) presence of theoretically predicted super atomic molecular orbitals,w hich are key factors for intermolecular charge/ energy transport distinct from the c...

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Corannulene derivatives for organic electronics: From molecular engineering to applications

Abstract: This review focuses on the recent progress in the functionalization of corannulenes and their applications in organic electronics.

Cited by 50 publications

References 96 publications

Crystal Engineering of Organic Optoelectronic Materials

Crystal Engineering of Organic Optoelectronic Materials

Highly nitrogen and sulfur dual-doped carbon microspheres for supercapacitors

Hierarchical Corannulene‐Based Materials: Energy Transfer and Solid‐State Photophysics

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