Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives:  The Brick and Mortar of Organic Electronics

Bendikov, Michael; Wudl, Fred; Perepichka, Dmitrii F.

doi:10.1021/cr030666m

Cited by 1,642 publications

(894 citation statements)

References 457 publications

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“…55-58°C). 1 A solution of 3 (817 mg, 4.44 mmol) in CH 2 Cl 2 (25 mL) was hydrogenated over 10 % Pd/C (59 mg) under atmospheric pressure at room temperature for 6 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Column chromatography (hexane) on silica gel afforded 4a (399 mg, 73 %) as a yellow oil, which was used in the next reaction without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…Column chromatography (hexane) on silica gel afforded 4a (399 mg, 73 %) as a yellow oil, which was used in the next reaction without further purification. 1 …”

Section: Methodsmentioning

confidence: 99%

“…The disubstituted furan 4b (1.05 g, 42 %) was obtained as a yellow oil and used in the next reaction without further purification. 1 Because 6a was apt to decompose on standing at room temp., it was used in the next reaction as soon as possible. A solution of 6a (234 mg, 0.55 mmol) in EtOH (55 mL) was hydrogenated over 10 % Pd/C (46 mg) under atmospheric pressure at room temperature for 4 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure.…”

Section: 5-diisobutylfuran (4b)mentioning

confidence: 99%

“…[1] However, they suffer from some disadvantages, such as their low solubility in solution, instability in air, and poor thinfilm morphologies, which limit their practical applications in low-cost device fabrication. Therefore many groups have increasingly performed acene functionalizations and reported various substituted oligoacenes.…”

Section: Introductionmentioning

confidence: 99%

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1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

et al. 2010

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We have synthesized 1,4,7,10-tetraisoalkyltetracenes from a 2,6-naphthodiyne precursor and 2,5-diisoalkylfurans as the starting materials (isoalkyl: isopropyl, isobutyl, and isopentyl). The tetracene molecules exhibited crystallochromy: The solid-state colors of the isopropyl, isobutyl, and isopentyl derivatives were yellow, red, and orange-yellow, respectively. In contrast, there were no marked differences in the optical properties of these compounds in solution. The isopropyl derivative exhibited the highest fluorescence quantum yield in

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Section: Methodsmentioning

confidence: 99%

“…Column chromatography (hexane) on silica gel afforded 4a (399 mg, 73 %) as a yellow oil, which was used in the next reaction without further purification. 1 …”

Section: Methodsmentioning

confidence: 99%

Section: 5-diisobutylfuran (4b)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

et al. 2010

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“…[1][2][3]. In recent years, new OSCs have been designed and improved through computational modeling [4][5][6] and virtual high-throughput screening [7][8][9].…”

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confidence: 99%

Coherent Dynamics of Mixed Frenkel and Charge-Transfer Excitons in Dinaphtho[2,3-b:2′3′-f]thieno[3,2-b]-thiophene Thin Films: The Importance of Hole Delocalization

Fujita

Atahan-Evrenk

Sawaya

et al. 2016

J. Phys. Chem. Lett.

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Charge transfer states in organic semiconductors play crucial roles in processes such as singlet fission and exciton dissociation at donor/acceptor interfaces. Recently, a time-resolved spectroscopy study of dinaphtho [2,3-b:2 ′ 3 ′ -f]thieno[3,2-b]-thiophene (DNTT) thin films provided evidence for the formation of mixed Frenkel and charge-transfer excitons after the photoexcitation. Here we investigate optical properties and excitation dynamics of the DNTT thin films by combining ab initio calculations and a stochastic Schrödinger equation. Our theory predicts that the low-energy Frenkel exciton band consists of 8 to 47% CT character. The quantum dynamics simulations show coherent dynamics of Frenkel and CT states in 50 fs after the optical excitation. We demonstrate the role of charge delocalization and localization in the mixing of CT states with Frenkel excitons as well as the role of their decoherence.Organic semiconductors (OSCs) are widely investigated as candidates for inexpensive and flexible materials for photovoltaics and other optoelectronic applications. [1][2][3]. In recent years, new OSCs have been designed and improved through computational modeling [4][5][6] and virtual high-throughput screening [7][8][9]. Modeling energy and charge transport properties is also essential for understanding structure-property relationships and thus for rationally designing novel OSCs [10][11][12][13][14][15][16].The low-energy optical excitations in OSCs lead to the formation of a bound electron-hole (e-h) pair, a Frenkel exciton. Excitonic properties of organic crystals are substantially different from those of isolated molecules, owing to excitonic couplings, near-field interactions between electronic transitions [17][18][19][20]. Interactions with a charge-transfer (CT) statea state in which the electron and hole are located on spatially separated regions-can also affect the optical properties of an exciton, as has been demonstrated by several theoretical studies [21][22][23][24][25][26]. Experimentally, the degree of CT character has been studied by momentum-dependent electron-loss spectroscopy [27][28][29] or electroabsorption spectroscopy [30][31][32]. CT states can act as precursors for interfacial CT states [33][34][35]; mixing of CT states with Frenkel excitons would facilitate charge separation in photovoltaic materials. They have also gained recent attention due to their relevance to singlet fission [36][37][38], in which singlet to triplet conversion can proceed via sequential CT steps [39][40][41].Here we focus on dinaphtho[2,3-b:, a p-type OSC originally introduced by Takimiya and co-workers [42]. DNTT and its derivatives [5,[43][44][45][46][47][48][49] have gained attention due to their high hole mobility values and air stability. A recent time-resolved spectroscopy study by Ishino et al. [48] concludes that mixed Frenkel and CT excitons are formed after the optical excitation. Although the degree of CT character in excited states has been reported as described in the earlier paragraph, its role in...

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Molecular Devices Based on Fullerenes and Carbon Nanotubes

Iurlo

Paolucci

Marcaccio

et al. 2009

Electrochemistry of Functional Supramolecular Systems

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Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: The Brick and Mortar of Organic Electronics

Cited by 1,642 publications

References 457 publications

1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

1,4,7,10‐Tetraisoalkyltetracenes: Tuning of Solid‐State Optical Properties and Fluorescence Quantum Yields by Peripheral Modulation

Coherent Dynamics of Mixed Frenkel and Charge-Transfer Excitons in Dinaphtho[2,3-b:2′3′-f]thieno[3,2-b]-thiophene Thin Films: The Importance of Hole Delocalization

Molecular Devices Based on Fullerenes and Carbon Nanotubes

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