Modular synthesis of asymmetric rylene derivatives

Sample, Caitlin S.; Goto, Eisuke; Handa, Nisha V.; Page, Zachariah A.; Luo, Yingdong; Hawker, Craig J.

doi:10.1039/c6tc05139a

Cited by 13 publications

(8 citation statements)

References 30 publications

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“…As depicted in Scheme 1, the key precursor 2 was obtained in 85 % yield via Stille coupling reaction of the starting materials 1 [12] and (E)‐1,2‐bis(tributyltin)ethylene. Subsequently, 2 underwent a photocyclization reaction with a catalytic amount of iodine afforded the PiDI in 94 % yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Stepwise Bromination, and Functionalization of Picene Diimide

Wang

Chen

et al. 2023

Chemistry A European J

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Materials Synthesis and Processing Polycyclic aromatic hydrocarbon (PAH) diimides are indispensable candidates for ntype organic semiconductors in organic optoelectronic devices. Developing new PAH diimide building blocks are of remarkable significance for material diversity and further advance in organic semiconductors. In this contribution, 4,5,8,9-picene diimide (PiDI) was designed and synthesized. Controllable stepwise bromination of PiDI were accomplished to afford 13-mono-bromo-, 13,14-dibromo-, 2,13,14-tribromo-and 2,11,13,14-tetrabromo-PiDI. Moreover, cyanation of 2,11,13,14-tetrabromo-PiDI gave the corresponding tetracyanated PiDI, which can be utilized as n-type semiconductor with OFET electron mobility up 0.073 cm 2 V À 1 s À 1 . This result demonstrates the potential of PiDI as a building block for constructing new high-performance electronic-transporting materials.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Stepwise Bromination, and Functionalization of Picene Diimide

Wang

Chen

et al. 2023

Chemistry A European J

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“…Although nature synthesizes asymmetric biomolecules with marvelous efficiencies 41 , it is a challenge for synthetic chemists to prepare asymmetric compounds due to poor selectivity and low yields 42 . In the case of n-type OSCs, several studies on the synthesis of asymmetric PDI have been reported [43][44][45] .…”

Section: Synthesismentioning

confidence: 99%

Molecular Mimicry and Assemblies of Asymmetric Organic Semiconductors

Kumagai

Tsutsumi

et al. 2021

Preprint

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Molecular assembly is a crucial factor for charge transports in organic semiconductors (OSCs), and molecularly flexible alkyl chain substitution is a key design feature for achieving desired molecular assemblies. However, the high degree of freedom of alkyl chains leads to molecular fluctuations that are detrimental to OSC performances. Stabilization of alkyl chains via intermolecular interactions in packing structures exists in biological and materials systems, and such a strategy can be harnessed in OSCs to suppress molecular fluctuations. Here, we present a robust synthetic strategy for a series of asymmetric n-type benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI) OSCs with various alkyl chain lengths, and certain alkyl chains exhibit an unusual molecular mimicry with energetically favorable gauche conformer that shows isomorphic structures and small molecular fluctuations. Asymmetric n-type OSC with the optimum chain length exhibits satisfactory solubility, excellent electron mobility, and large-area single-crystalline thin films are fabricated for practical organic electronics.

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Section: Introductionmentioning

confidence: 99%

“…To address these limitations, PBI cores were modified with various substituents on their imide nitrogen atoms (N-substitution, X) or on bay-region positions (bay-modifications, Y), or by cracking the C-C bond of the PBI backbone to create bisnaphthalimide (BNI) derivatives (Scheme 1). [13][14][15][16][17][18][19][20] PBIs substituted with dendrons at the bay and/or imide positions can self-organize into 2D and 3D columnar periodic arrays [21][22][23][24][25][26][27][28] exhibiting high charge carrier mobility of interest for photovoltaic and other electronic applications. For example, novel classes of complex helical columns assembled from (3,4,5)nG1-m-PBI substituted with dendrons containing 0-4 methylenic units (m) between the imide group of the dendrons and 6-12 methylenic units (n) in their alkyl groups were reported by Percec et al (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%