Substituted dibenzo[2,3:5,6]-pyrrolizino[1,7-bc]indolo[1,2,3-lm]carbazoles: a series of new electron donors

Rivoal, Morgane; Bekere, Laura; Gachet, D.; Lokshin, Vladimir; Marine, W.; Khodorkovsky, Vladimir

doi:10.1016/j.tet.2013.02.007

Cited by 17 publications

(14 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the UV region, the prominent absorption peaks for DMDBIC compound are obtained at 324 nm (f=0.40), 308 nm (f=0.27), and 265 nm (f=0.33) associated with the electronic transitions H‐1→L, H‐1→L+1, and H‐3→L+1, respectively. Similarly, the absorption spectra of DMDPIC compound appearing in the visible range (400 nm ‐ 550 nm) is found to be in good agreement with the results reported by Rivoal et al . The 1st prominent peak associated with lowest energy transitions (S 0 →S 1 ) is obtained at around 463 nm.…”

Section: Resultssupporting

confidence: 90%

“…The calculated absorption spectra at the B3LYP level are shown in Figure and the corresponding absorption wavelengths (λ abs ), oscillator strengths (f), transition energy (E), and the electronic transitions are summarized in Table . We have also calculated the absorption spectra of the studied compounds using M06 functional and noted that spectra at both B3LYP and M06 levels of theory are similar and in good agreement with the reported experimental results ,. However, for the sake of brevity, we only discuss the results computed at B3LYP/6‐311+G (d,p) level.…”

Section: Resultssupporting

confidence: 66%

“…The optimized and experimental structural parameters such as; bond lengths and bond angles for DIC, DMDBIC, and DMDPIC are listed in Table S1 ‐ S6. The calculated bond lengths and angles at the above‐mentioned level of theory are found to be in good agreement with the crystal structure ,,. As assured in Table S1 ‐ S6, the maximum deviation in optimized bond lengths with respect to the experimental bond lengths are 0.016 Å, 0.013 Å, and 0.0147 Å for DIC, DMDBIC, and DMDPIC compounds, respectively.…”

Section: Resultssupporting

confidence: 66%

“…The calculated bond lengths and angles at the abovementioned level of theory are found to be in good agreement with the crystal structure. [48,49,50] As assured in Table S1 -S6, the maximum deviation in optimized bond lengths with respect to the experimental bond lengths are 0.016 Å, 0.013 Å , and 0.0147 Å for DIC, DMDBIC, and DMDPIC compounds, respectively. The change in bond length between the neutral, cationic and anionic geometries of three IC derivatives calculated at the B3LYP/6-311 + G(d,p) level are depicted in Figure 2.…”

Section: Geometrical Propertiesmentioning

confidence: 82%

“…Computation The initial geometries were obtained from the reported crystal structures of DIC (CCDC 940861), DMDBIC (CCDC 982170), and DMDPIC (CCDC 905655) listed in Cambridge Crystallographic Data Center. [48,49,50] We optimized the neutral and ionic state molecular geometries of the above IC derivatives using B3LYP hybrid exchange-correlation functional and 6-311 + G(d,p) basis sets within the framework of density functional theory (DFT). In addition, to incorporate the long-range correction, the molecules were also optimized using the range separated functional wB97XD which includes empirical dispersion.…”

Section: Theory and Computation Theorymentioning

confidence: 99%

See 4 more Smart Citations

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

2018

View full text Add to dashboard Cite

We present a detailed theoretical study of the structural, charge transport, and optical properties of three indolocarbazole derivatives, viz., 11, 12‐Dihydroindolo[2, 3‐a]carbazole (DIC), 5, 10‐dimethyl‐5,10‐dihydrobenzo[a]indolo[2, 3‐c]carbazole (DMDBIC), and 2,11‐dimethoxydibenzo[2, 3:5,6]pyrrolizino[1, 7‐bc]indolo[1, 2,3‐lm]carbazole (DMDPIC). DFT calculations along with previously reported x‐ray crystal structures reveal that the studied compounds are planar and do not undergo significant changes in structure upon oxidation or reduction. The maximum hole anisotropic charge mobilities for DIC was found to be 0.338 cm2 V−1 s−1 at Φ=175.89° and 355.81° and the maximum electron mobility was 0.181 cm2 V−1 s−1 at Φ=85.94° and 265.85°. For DMDBIC, the predicted maximum anisotropic hole, and electron mobility was 0.501 cm2 V−1 s−1 and 0.775 cm2 V−1 s−1, respectively at Φ=56.72° and 236.63°, while for DMDPIC the predicted maximum anisotropic hole and electron mobility as 1.586 cm2 V−1 s−1 and 0.594 cm2 V−1 s−1, respectively at Φ=0° and 180.0°. The calculated mobilities show that these compounds may be suitable candidates as a p‐type organic semiconductor with better stability than acene compounds.

show abstract

Section: Resultssupporting

confidence: 90%

Section: Resultssupporting

confidence: 66%

Section: Resultssupporting

confidence: 66%

Section: Geometrical Propertiesmentioning

confidence: 82%

Section: Theory and Computation Theorymentioning

confidence: 99%

See 3 more Smart Citations

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

2018

View full text Add to dashboard Cite

show abstract

Strained Dehydrogenative Ring Closure of Phenylcarbazoles

2015

View full text Add to dashboard Cite

What does it take to force a rigid and strained dehydrogenative ring closure, for example, in phenylcarbazoles? Since the works of Buchwald and Fagnou, palladium‐catalysed ring‐closing dehydrogenative reactions are legion, but will not operate when the strain at the reductive elimination stage becomes too large. We propose here a “muscled up” super‐oxidative palldium‐catalysed CH activation method for the ring closure of strained phenylcarbazoles.magnified image

show abstract

An Ideal Molecular Construction Strategy for Ultra‐Narrow‐Band Deep‐Blue Emitters: Balancing Bathochromic‐Shift Emission, Spectral Narrowing, and Aggregation Suppression

Luo,

Jin,

et al. 2023

Advanced Science

View full text Add to dashboard Cite

Narrowband emissive multiple resonance (MR) emitters promise high efficiency and stability in deep‐blue organic light‐emitting diodes (OLEDs). However, the construction of ideal ultra‐narrow‐band deep‐blue MR emitters still faces formidable challenges, especially in balancing bathochromic‐shift emission, spectral narrowing, and aggregation suppression. Here, DICz is chosen, which possesses the smallest full‐width‐at‐half‐maximum (FWHM) in MR structures, as the core and solved the above issue by tuning its peripheral substitution sites. The 1‐substituted molecule Cz‐DICz is able to show a bright deep‐blue emission with a peak at 457 nm, an extremely small FWHM of 14 nm, and a CIE coordinate of (0.14, 0.08) in solution. The corresponding OLEDs exhibit high maximum external quantum efficiencies of 22.1%–25.6% and identical small FWHMs of 18 nm over the practical mass‐production concentration range (1–4 wt.%). To the best of the knowledge, 14 and 18 nm are currently the smallest FWHM values for deep‐blue MR emitters with similar emission maxima under photoluminescence and electroluminescence conditions, respectively. These discoveries will help drive the development of high‐performance narrowband deep‐blue emitters and bring about a revolution in OLED industry.

show abstract

Substituted dibenzo[2,3:5,6]-pyrrolizino[1,7-bc]indolo[1,2,3-lm]carbazoles: a series of new electron donors

Cited by 17 publications

References 25 publications

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

Indolocarbazole (IC) Derivatives as Promising p‐type Organic Semiconductors: A First‐Principle Study of Their Anisotropic Charge Mobilities

Strained Dehydrogenative Ring Closure of Phenylcarbazoles

An Ideal Molecular Construction Strategy for Ultra‐Narrow‐Band Deep‐Blue Emitters: Balancing Bathochromic‐Shift Emission, Spectral Narrowing, and Aggregation Suppression

Contact Info

Product

Resources

About