2022
DOI: 10.1002/ange.202200779
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Pushing the Length Limit of Dihydrodiboraacenes: Synthesis and Characterizations of Boron‐Embedded Heptacene and Nonacene

Abstract: Boron-embedded heteroacenes (boraacenes) have attracted enormous interest in organic chemistry and materials science. However, extending the skeleton of boraacenes to higher acenes (N � 6) is synthetically challenging because of their limited stability under ambient conditions. Herein, we report the synthesis of boron-embedded heptacene (DBH) and nonacene (DBN) as the hitherto longest boraacenes. The former is highly stable (even after 240 h in tetrahydrofuran), while the latter is air-sensitive with the half-… Show more

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Cited by 8 publications
(7 citation statements)
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“…Normally, photoluminescence of organic molecules originates from only the lowest excited state of a given spin multiplicity and is irrespective of the excitation wavelength, which is also known as Kasha’s rule . The significant overlap between the weak absorption band over 400 nm and fluorescence exhibits the possibility of anti-Kasha emissions (Figure c), which is also in agreement with the forbidden S 0 → S 1 and S 0 → S 2 transitions calculated by TD-DFT (Section S7 in SI). , To further investigate the anti-Kasha emission behaviors of 1-C5 , 1-C10 , and 1-Mes , the excitation-wavelength-dependent fluorescence and phosphorescence spectra (Figure b,d and Section S5 in SI) and emission-wavelength-dependent excitation spectra (Figure c and Section S5 in SI) were exploited. Different solvents were tested to exclude the influence of solvents on the anti-Kasha emission phenomenon (Figures S26–S34 in SI). As shown in Figure b, the right shoulder intensity at 410 nm of the emission of 1-Mes was increased when the excitation wavelength was changed from 350 to 370 nm.…”
supporting
confidence: 60%
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“…Normally, photoluminescence of organic molecules originates from only the lowest excited state of a given spin multiplicity and is irrespective of the excitation wavelength, which is also known as Kasha’s rule . The significant overlap between the weak absorption band over 400 nm and fluorescence exhibits the possibility of anti-Kasha emissions (Figure c), which is also in agreement with the forbidden S 0 → S 1 and S 0 → S 2 transitions calculated by TD-DFT (Section S7 in SI). , To further investigate the anti-Kasha emission behaviors of 1-C5 , 1-C10 , and 1-Mes , the excitation-wavelength-dependent fluorescence and phosphorescence spectra (Figure b,d and Section S5 in SI) and emission-wavelength-dependent excitation spectra (Figure c and Section S5 in SI) were exploited. Different solvents were tested to exclude the influence of solvents on the anti-Kasha emission phenomenon (Figures S26–S34 in SI). As shown in Figure b, the right shoulder intensity at 410 nm of the emission of 1-Mes was increased when the excitation wavelength was changed from 350 to 370 nm.…”
supporting
confidence: 60%
“…43 The significant overlap between the weak absorption band over 400 nm and fluorescence exhibits the possibility of anti-Kasha emissions (Figure 3c), which is also in agreement with the forbidden S 0 → S 1 and S 0 → S 2 transitions calculated by TD-DFT (Section S7 in SI). 44,45 To further investigate the anti-Kasha emission behaviors of 1-C5, 1-C10, and 1-Mes, the excitationwavelength-dependent fluorescence and phosphorescence spectra (Figure 4b,d and Section S5 in SI) and emissionwavelength-dependent excitation spectra (Figure 4c and Section S5 in SI) were exploited. 45−47 Different solvents were tested to exclude the influence of solvents on the anti-…”
Section: T H Imentioning
confidence: 99%
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“…The boron atom has an empty p orbital, which enables it to serve as a strong electron acceptor. 15 Along with the unique electronic properties of the boron atom, organoboron compounds, especially π-conjugated boron embedded molecules, are widely investigated in chemical sensors, 16 organic synthesis, 17 optoelectronic materials, 18 and spin carriers. 19 The N,C-chelate boron compounds BN1 and BN3 are highly sensitive to light: BN1 and its derivatives can undergo efficient reversible photoisomerization; 20 BN3 and its derivatives can form azaborines 21 via photoelimination upon UV light irradiation.…”
Section: Introductionmentioning
confidence: 99%
“…The significant overlap between the week absorption bands over 400 nm and fluorescence exhibits the possibility of anti-Kasha emissions, which is also in agreement with the forbidden S 0 -S 1 and S 0 -S 2 transitions calculated by TD-DFT (Figure 5a). 40,41 Normally, photoluminescence of organic molecules originates from only the lowest excited state of a given spin multiplicity and is irrespective of the excitation wavelength, which is also known as the Kasha's rule. 42 To further investigate the anti-Kasha emission behaviors of 1-C5, 1-C10 and 1-Mes, the excitation-wavelength-dependent fluorescence and phosphorescence spectra (Figure 5b, 5d and Figure S13, S14a and S15a in SI) and emission-wavelengthdependent excitation spectra (Figure 5c, and Figure S14b and S15b in SI) were exploited.…”
mentioning
confidence: 99%