High-Performance Organic Electronic Materials by Contorting Perylene Diimides

Schaack, Cédric; Evans, Austin M.; Ng, Fay; Steigerwald, Michael L.; Nuckolls, Colin

doi:10.1021/jacs.1c11544

Cited by 62 publications

(51 citation statements)

References 56 publications

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“…For example, the PDI-end-capped series showed strong circular dichroism (CD) responses and encouraging absorption dissymmetry factor ( g abs = Δε/ε) larger than 10 –2 . Although they exhibited good Φ PL in the range of 27%–68%, the corresponding g lum factor has not been evaluated yet. , In contrast, the PDI-embedded superhelicenes (i.e., 23 and 24 ) feature two helical wings located on the upper and lower sides or the same side of the PDI plane. Both of them possessed good fluorescence efficiencies with a Φ PL value of approximately 30%.…”

Section: Functional Landscapesmentioning

confidence: 99%

Molecular Carbon Imides

Wang

2022

J. Am. Chem. Soc.

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The creation and development of new forms of nanocarbons have fundamentally transformed the scientific landscape in the past three decades. As new members of the nanocarbon family with accurate size, shape, and edge structure, molecular carbon imides (MCIs) have shown unexpected and unique properties. Particularly, the imide functionalization strategy has endowed these rylene-based molecular carbons with fascinating characteristics involving flexible syntheses, tailor-made structures, diverse properties, excellent processability, and good stability. This Perspective elaborates molecular design evolution to functional landscapes, and illustrative examples are given, including a promising library of multi-size and multi-dimensional MCIs with rigidly conjugated π-architectures, ranging from 1D nanoribbon imides and 2D nanographene imides to cross-dimensional MCIs. Although researchers have achieved substantial progress in using MCIs as functional components for exploration of charge transport, photoelectric conversion, and chiral luminescence performances, they are far from unleashing their full potential. Developing highly efficient and regioselective coupling/ring-closure reactions involving the formation of multiple C–C bonds and the annulation of electron-deficient aromatic units is crucial. Prediction by theory with the help of machine learning and artificial intelligence research along with reliable nanotechnology characterization will give an impetus to the blossom of related fields. Future investigations will also have to advance towardor even focus onthe emerging potential functions, especially in the fields of chiral electronics and spin electronics, which are expected to open new avenues.

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Section: Functional Landscapesmentioning

confidence: 99%

Molecular Carbon Imides

Wang

2022

J. Am. Chem. Soc.

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“…Perylene diimide (PDI) is a unique class of chromophores that features extensive and intensive absorption in the visible light region, outstanding luminescent ability, structural modifiability, and thermo-optical stability. − In this study, we selected it as a substructure to construct such a tetrarylene-based double π-helix (namely TH molecules): (i) the extremely rigid ladder framework endows these molecules a high isomerization barrier, (ii) using PDI as a substructure is beneficial to a superior molar extinction coefficient (ε) and Φ PL , and (iii) heteroannulation at the vacant bay region could further accommodate transition dipole moments μ and m to a large extent; in brief, a high g lum ( g lum = 4cosθ| m |/| μ |) and eventually an excellent CPL brightness according to the proposed equation ( B CPL = ε λ × Φ PL × | g lum |/2) could be achieved (Figure ). Based on the design concept, we elaborated a series of TH molecules resulting from cyclooctatetraene-embedded perylene diimide dimer associated with their efficient CPL performances, in which the magnitudes of μ and m for their S 1 –S 0 transitions were unequivocally elucidated and further regulated by heteroannulation.…”

Section: Introductionmentioning

confidence: 99%

Boosting Circularly Polarized Luminescence Performance by a Double π-Helix and Heteroannulation

Liu

Wang

et al. 2022

J. Am. Chem. Soc.

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Design challenges in the development of circularly polarized luminescence (CPL) materials are focused on balancing the luminescence dissymmetry factor (g lum) and photoluminescence quantum yield (ΦPL) by regulating the electric ( μ ) and magnetic ( m ) transition dipole moment vectors. Aiming at designing efficient CPL emitters and clarifying the chiroptical variation mechanism, herein, we present a double π-helix based on a cyclooctatetraene-embedded perylene diimide dimer that combines chirality with molecular entanglement and very high barriers for racemization. Through finely regulating the magnitudes of μ and m , the maximal dissymmetry factors |g abs| and |g lum| can be boosted to 0.035 and 0.030, respectively, as revealed by circular dichroism (CD) and CPL spectra. The results indicate a 3-fold improvement of g values and a modulated ΦPL from 1a, 4, to 5 by nitrogen heteroannulation at the bay region. The CPL brightness (B CPL) of 5 reaches a recorded value of up to 573.4 M–1 cm–1, among the highest values of chiral small molecules reported so far. This work has provided a comprehensive insight into a new class of chiral materials with high CPL activities, further laying molecular fundamentals for chiral optoelectronics.

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“…Despite their peculiar properties, however, helicenes still remain rather unexplored in solid-state (opto-)electronic devices. Racemic mixtures of tetrathia-[7]-helicene [ 27 ], naphthalene double [6]helicenes [ 28 ], pyrene double [4]heterohelicene [ 29 ], 5,14-diaryldiindeno[2,1-f:1′,2′-j]picene [ 30 , 31 ], perylene diimide double-[5]heterohelicene [ 32 , 33 ], and a multiple helicene containing two [5]helicene and four [4]helicene moieties [ 34 ] have been used in organic thin-film transistors (OTFTs). Some authors exploited the chirality of the helicenes by using the enantiomerically pure 1-aza[6]helicene [ 35 ] and perylene diimide double-[7]heterohelicene [ 36 ] in circularly polarized detecting OTFTs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Thin-Film Transistor Response of Benzo[i]pentahelicene-3,6-dione

Bracciale

Kwon

et al. 2022

Molecules

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Organic semiconductors hold the promise of simple, large area solution deposition, low thermal budgets as well as compatibility with flexible substrates, thus emerging as viable alternatives for cost-effective (opto)-electronic devices. In this study, we report the optimized synthesis and characterization of a helically shaped polycyclic aromatic compound, namely benzo[i]pentahelicene-3,6-dione, and explored its use in the fabrication of organic field effect transistors. In addition, we investigated its thermal, optical absorption, and electrochemical properties. Finally, the single crystal X-ray characterization is reported.

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High-Performance Organic Electronic Materials by Contorting Perylene Diimides

Cited by 62 publications

References 56 publications

Molecular Carbon Imides

Molecular Carbon Imides

Boosting Circularly Polarized Luminescence Performance by a Double π-Helix and Heteroannulation

Synthesis, Characterization, and Thin-Film Transistor Response of Benzo[i]pentahelicene-3,6-dione

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