Evaluating the Impact of Fluorination on the Electro-optical Properties of Cross-Conjugated Benzobisoxazoles

Chavez, Ramiro; Diodati, Lily; Wheeler, David L.; Shaw, Jessica; Tomlinson, Aimée L.; Jeffries‐EL, Malika

doi:10.1021/acs.jpca.8b07778

Cited by 9 publications

(11 citation statements)

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“…The dihedral angle between the BBO moiety and the aryl substituents is an indication of planarity within these systems. 10 substituents is negligible along the 2,6-axis. However, the steric effects are significant when the aryl groups are placed along the 4,8-axis as 48M (157.1°) is significantly less planar than 48P (174.2°).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…All benchmarking efforts and results, which led to the chosen functional and basis set, are outlined in previous work. 10 Electronic ground-state geometries were optimized using density functional theory (DFT), employing the mPW3PBE functional and the SV basis set verified through a frequency calculation both with and without chloroform inclusion through the conductor polarizable calculation model (CPCM). Excited states for both phases were generated through time-dependent density functional theory (TD-DFT) applied to the optimized ground state for each oligomer.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

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Evaluating the Role of Molecular Heredity in the Optical and Electronic Properties of Cross-Conjugated Benzo[1,2-d:4,5-d′]bisoxazoles

et al. 2020

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A series of eight benzo [1,2-d:4,5-d′]bisoxazole (BBOs) were synthesized using the heredity principle as a design motif, whereby we investigated which characteristics of the linear parents were inherited by their cross-conjugated children. Four linear parents bearing 4-tert-butylbenzene (P) or 1,3-bis(4-tertbutylphenyl)benzene (M) at either the 2,6-or 4,8-position on the BBO and four cross-conjugated children bearing various combinations of the two isoelectronic aryl substituents were evaluated. Due to the bulky nature of the M substituent compared to that of the P substituent, the influence of steric hindrance along the BBO axes was explored theoretically and experimentally. The optical and electronic properties of each molecule were investigated in the solution and solid state using density functional theory (DFT) and time-dependent DFT (TD-DFT) and characterized using ultraviolet photoelectron spectroscopy (UPS), ultraviolet−visible (UV−vis) spectroscopy, and photoluminescence (PL) spectroscopy. The well-correlated theoretical and experimental results showed that the selective tuning of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels was possible through the strategic placement of substituents without impacting the H → L transition energy. Specifically, the theoretical results demonstrated that for the BBO children the HOMO and LUMO energy levels were inherited from the 4,8-and 2,6-parents, respectively. Each molecule was found to exhibit emission maxima ≤451 nm, making them ideal candidates for blue organic light-emitting diode (OLED) materials.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Experimental Sectionmentioning

confidence: 99%

Evaluating the Role of Molecular Heredity in the Optical and Electronic Properties of Cross-Conjugated Benzo[1,2-d:4,5-d′]bisoxazoles

et al. 2020

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“…The faculty published 2 peer‐reviewed books, [ 238,239 ] 9 peer‐reviewed book chapters, [ 240–248 ] and 115 peer‐reviewed research papers. [ 249–363 ] This comes to 1.6 peer‐reviewed products/faculty/year during the 3‐year grant period, which is 3.2 times the rate of publication for natural science faculty at PUIs. [ 46 ]…”

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Twenty years of exceptional success: The molecular education and research consortium in undergraduate computational chemistry (MERCURY)

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2020

Int J of Quantum Chemistry

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The molecular education and research consortium in undergraduate computational chemistry (MERCURY) consortium, established in 2000, has contributed greatly to the scientific development of faculty and undergraduates. The MERCURY faculty peer-reviewed publication rate from 2001 to 2019 of 1.7 papers/faculty/year is 3.4 times the rate of the physical science faculty at primarily undergraduate institutions. We have worked with over 1000 students on research projects since 2001, and 75% of our undergraduate research students have been under-represented in chemistry, either female or students of color. Approximately half of our alumni attend graduate school for the purpose of obtaining advanced degrees in STEM fields, and two-thirds are female and/or students of color. We have had more than 1600 attendees at 18 MERCURY conferences, including 111 invited speakers, 61 of whom have been female and/or faculty of color. In this paper, the research accomplishments, transformational outcomes, and scientific productivity of the MERCURY faculty are highlighted.

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“…Our group has focused on the development of novel organic semiconductors based on benzobis[1,2-d;4,5-d']oxazole (BBOs) cruciforms and their application in organic electronics. [17][18][19][20][21] These materials are comprised of four aryl-substituents along the central benzene ring (4,8-(2,6-position/axis), Figure 1. 22,23 This arrangement creates spatially segregated frontier molecular orbitals (FMOs), facilitating the nearly independent tuning of the HOMO and LUMO levels, respectively using aromatic substitution.…”

Section: Introductionmentioning

confidence: 99%

A computational and experimental investigation of deep-blue light-emitting tetraaryl-benzobis[1,2-d:4,5-d′]oxazoles

et al. 2022

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Evaluating the Impact of Fluorination on the Electro-optical Properties of Cross-Conjugated Benzobisoxazoles

Abstract: OpenBU http://open.bu.edu Chemistry BU Open Access Articles 2019-02-21 Evaluating the impact of fluorination on the electro-optical properties of cross-conjuga...

Cited by 9 publications

References 34 publications

Evaluating the Role of Molecular Heredity in the Optical and Electronic Properties of Cross-Conjugated Benzo[1,2-d:4,5-d′]bisoxazoles

Evaluating the Role of Molecular Heredity in the Optical and Electronic Properties of Cross-Conjugated Benzo[1,2-d:4,5-d′]bisoxazoles

Twenty years of exceptional success: The molecular education and research consortium in undergraduate computational chemistry (MERCURY)

A computational and experimental investigation of deep-blue light-emitting tetraaryl-benzobis[1,2-d:4,5-d′]oxazoles

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