Strongly red-fluorescent novel donor–π-bridge–acceptor–π-bridge–donor (D–π–A–π–D) type 2,1,3-benzothiadiazoles with enhanced two-photon absorption cross-sections

Kato, Shin‐ichiro; Matsumoto, Taisuke; Ishi‐i, Tsutomu; Thiemann, Thies; Shigeiwa, Motoyuki; Gorohmaru, Hideki; Maeda, Shuichi; Yamashita, Yoshiro; Mataka, Shuntarō

doi:10.1039/b410016f

Cited by 167 publications

(95 citation statements)

References 18 publications

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“…Compound 1: A solution of 9,10-dibromoanthracene (157.9 mg, 0.47 mmol), 3,6-di-tert-butyl-9-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (500 mg, 1.04 mmol), Pd(PPh 3 ) 4 (55 mg, 0.05 mmol), aqueous K 2 CO 3 (2 , 6 mL, 11.6 mmol), PPh 3 (40 mg, 0.15 mmol), and aliquat 336 (2 drops) in toluene (30 mL) was heated at reflux for 24 h. The mixture was quenched with water after cooling back to room temperature and extracted with dichloromethane. The combined organic extracts were dried with anhydrous Na 2 …”

Section: Methodsmentioning

confidence: 99%

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Selective Tuning of the HOMO–LUMO Gap of Carbazole‐Based Donor–Acceptor–Donor Compounds toward Different Emission Colors

et al. 2010

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Carbazole‐based donor–acceptor compounds with tunable HOMO–LUMO gaps were synthesized by Suzuki and Sonogashira cross‐coupling reactions. Their optical and electrochemical properties were fully characterized. The results show that materials with different emission colors ranging from blue to green to orange could be obtained. The experimental results were also supported by theoretical calculations.

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Section: Methodsmentioning

confidence: 99%

“…[3,4] The EL and NLO performances of these molecules are effectively dependent on their HOMO-LUMO or band gaps associated with intramolecular D-A interactions. The strength of D-A interactions is determined by donor and acceptor groups and the connecting π bridges.…”

Section: Introductionmentioning

confidence: 99%

Selective Tuning of the HOMO–LUMO Gap of Carbazole‐Based Donor–Acceptor–Donor Compounds toward Different Emission Colors

et al. 2010

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“…Due to its strong electron-withdrawing ability [8], the spectral properties of BTD could be easily modulated by chemical environment. We then first investigated the absorption spectra of 1 and 2 in HEPES buffer solution at pH 7.4.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

“…Benzothiadiazoles (BTD) with good optical properties and strong electron-withdrawing characters have attracted much attention due to their potential applications in organic functional materials [1][2][3][4][5][6][7][8][9][10]. For instance, when coupled with N,N-diaryl N terminus via various p-conjugate spacers, the corresponding BTD derivatives exhibited large twophoton absorption in orange-red color [8].…”

Section: Introductionmentioning

confidence: 99%

“…For instance, when coupled with N,N-diaryl N terminus via various p-conjugate spacers, the corresponding BTD derivatives exhibited large twophoton absorption in orange-red color [8]. While being incorporated into conjugate polymer, BTD could modulate the photophysical properties of polymer which had great importance in organic optical-electrical materials [11][12][13].…”

Section: Introductionmentioning

confidence: 99%

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Cooperative recognition of Cu2+ based on amino acids tethered benzothiadiazoyl-bistriazoles

Ruan¹,

Maisonneuve²,

et al. 2010

Front. Chem. China

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New Construction of Low‐Bandgap Conducting Polymers

Zhu¹,

Waller²,

Brabec³

2008

Organic Photovoltaics

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IntroductionConducting polymers [1] are organic polymeric materials that possess electronic properties similar to those of metals or inorganic semiconductors. They surpass their inorganic counterparts in solubility and processibility, which makes possible the fabrication of exceptionally thin devices, promising revolutionary advancements in many technologies such as flexible and large-area displays [1-3], field effect transistors [4][5][6], and photovoltaics [7][8][9]. Polyacetylene, the first conducting polymer, was discovered in the 1970s [10,11]. After that, many new conducting polymers were soon synthesized and the scope of this class of material was quickly expanded to include the poly(arylenene), poly(arylene vinylene), and poly(arylene ethynylenes), where the arylenes are pyrrole, benzene, or thiophene. Incorporation of arylenes into the polymer chains affords more stable polymers and also provides anchoring points for side chains, offering additional control of polymer properties such as solubility. As conducting polymers continued to evolve, more sophisticated aromatic units such as fluorenes were incorporated into the main chains and various polymer and copolymers were developed (Figure 4.1(3)) [12]. One interesting feature of fluorene is that its 9-carbon can be readily functionalized with alkyl groups to increase the solubility of the polymer without causing additional twist in the main chain. For the past 10 years, both main chains and side chains are being constantly diversified giving rise to numerous structures and rich combinations of properties, providing an increasingly clear picture of structure-property relationship and allowing for more efficient design and optimization of structures to address various application needs. One of the most important characteristics of a conducting polymer is its bandgap, which is defined as the energy difference between the HOMO and LUMO of a polymer. A small bandgap is desired for increasing the conductivity and enhancing the nonlinear optical properties of the polymers [13,14]. Also, a small bandgap allows the material to absorb light up to a longer wavelength, which is highly desired for photovoltaic applications, where a good coverage of the solar spectrum is required for

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Strongly red-fluorescent novel donor–π-bridge–acceptor–π-bridge–donor (D–π–A–π–D) type 2,1,3-benzothiadiazoles with enhanced two-photon absorption cross-sections

Cited by 167 publications

References 18 publications

Selective Tuning of the HOMO–LUMO Gap of Carbazole‐Based Donor–Acceptor–Donor Compounds toward Different Emission Colors

Selective Tuning of the HOMO–LUMO Gap of Carbazole‐Based Donor–Acceptor–Donor Compounds toward Different Emission Colors

Cooperative recognition of Cu2+ based on amino acids tethered benzothiadiazoyl-bistriazoles

New Construction of Low‐Bandgap Conducting Polymers

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