Ab Initio Calculations on Structure and Stability of BN/CC Isosterism in Azulene

Overview

Journal Sci Rep

Specialty Science

Date 2023 Jun 24

PMID 37355719

Authors

Mohamed A Abdel-Rahman

Kamal A Soliman

Safwat Abdel-Azeim

Ahmed M El-Nahas

Tetsuya Taketsugu

Takahito Nakajima

Asmaa B El-Meligy

Affiliations

Soon will be listed here.

Abstract

Herein, we investigated the thermodynamic stability and opto-electronic properties of a newly BN-doped azulene. The gas-phase formation enthalpies of 11 BN-doped azulene were calculated by the atomization energy method using three computational models (CBS-APNO, CBS-QB3, and G3MP2). The results suggest that AZ-1N9B exhibits the highest stability among the studied isomers. On the other hand, AZ-1B9N and AZ-9B10N display nearly equal stability with relative energies of 19.36 and 19.82 kcal/mol at CBS-QB3, respectively. These two isomers are considered the least stable among the investigated compounds. The frontier molecular orbitals (FMO), ionization energies (IE), and electron affinities (EA) of these isomers were discussed. Additionally, the electronic absorption spectra of the BN-doped azulenes were computed using the TD-B3LYP/6-31 + G(d,p) and TD-CAM-B3LYP level of theories, which using a long-range corrected hybrid functional in acetone. The computational results obtained in this research are align closely with the existing literature, thereby reinforcing the credibility and reliability of our findings.

References

Veys K, Escudero D . Computational Protocol To Predict Anti-Kasha Emissions: The Case of Azulene Derivatives. J Phys Chem A. 2020; 124(36):7228-7237. DOI: 10.1021/acs.jpca.0c05205. View

Liu Z, Ishibashi J, Darrigan C, Dargelos A, Chrostowska A, Li B . The Least Stable Isomer of BN Naphthalene: Toward Predictive Trends for the Optoelectronic Properties of BN Acenes. J Am Chem Soc. 2017; 139(17):6082-6085. DOI: 10.1021/jacs.7b02661. View

Zhang G, Musgrave C . Comparison of DFT methods for molecular orbital eigenvalue calculations. J Phys Chem A. 2007; 111(8):1554-61. DOI: 10.1021/jp061633o. View

Yu H, He X, Li S, Truhlar D . MN15: A Kohn-Sham global-hybrid exchange-correlation density functional with broad accuracy for multi-reference and single-reference systems and noncovalent interactions. Chem Sci. 2018; 7(8):5032-5051. PMC: 6018516. DOI: 10.1039/c6sc00705h. View

Grimme S, Antony J, Ehrlich S, Krieg H . A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010; 132(15):154104. DOI: 10.1063/1.3382344. View

Grimme S, Ehrlich S, Goerigk L . Effect of the damping function in dispersion corrected density functional theory. J Comput Chem. 2011; 32(7):1456-65. DOI: 10.1002/jcc.21759. View

Pettersen E, Goddard T, Huang C, Meng E, Couch G, Croll T . UCSF ChimeraX: Structure visualization for researchers, educators, and developers. Protein Sci. 2020; 30(1):70-82. PMC: 7737788. DOI: 10.1002/pro.3943. View

Kurotobi K, Kim K, Noh S, Kim D, Osuka A . A quadruply azulene-fused porphyrin with intense near-IR absorption and a large two-photon absorption cross section. Angew Chem Int Ed Engl. 2006; 45(24):3944-7. DOI: 10.1002/anie.200600892. View

OBoyle N, Tenderholt A, Langner K . cclib: a library for package-independent computational chemistry algorithms. J Comput Chem. 2007; 29(5):839-45. DOI: 10.1002/jcc.20823. View

10.

Ito S, Inabe H, Morita N, Ohta K, Kitamura T, Imafuku K . Synthesis of poly(6-azulenylethynyl)benzene derivatives as a multielectron redox system with liquid crystalline behavior. J Am Chem Soc. 2003; 125(6):1669-80. DOI: 10.1021/ja0209262. View

11.

Schmitt S, Baumgarten M, Simon J, Hafner K . 2,4,6,8-Tetracyanoazulene: A New Building Block for "Organic Metals". Angew Chem Int Ed Engl. 2018; 37(8):1077-1081. DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1077::AID-ANIE1077>3.0.CO;2-R. View

12.

Perdew J, Ruzsinszky A, Tao J, Staroverov V, Scuseria G, Csonka G . Prescription for the design and selection of density functional approximations: more constraint satisfaction with fewer fits. J Chem Phys. 2005; 123(6):62201. DOI: 10.1063/1.1904565. View

13.

Tawada Y, Tsuneda T, Yanagisawa S, Yanai T, Hirao K . A long-range-corrected time-dependent density functional theory. J Chem Phys. 2004; 120(18):8425-33. DOI: 10.1063/1.1688752. View

14.

Chai J, Head-Gordon M . Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys. 2008; 10(44):6615-20. DOI: 10.1039/b810189b. View

15.

Lee , Yang , PARR . Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B Condens Matter. 1988; 37(2):785-789. DOI: 10.1103/physrevb.37.785. View

16.

Grimme S . Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem. 2006; 27(15):1787-99. DOI: 10.1002/jcc.20495. View

17.

Nagarajan N, Velmurugan G, Prakash A, Shakti N, Katiyar M, Venuvanalingam P . Highly emissive luminogens based on imidazo[1,2-a]pyridine for electroluminescent applications. Chem Asian J. 2013; 9(1):294-304. DOI: 10.1002/asia.201301061. View

18.

Morgan M, Piers W . Efficient synthetic methods for the installation of boron-nitrogen bonds in conjugated organic molecules. Dalton Trans. 2015; 45(14):5920-4. DOI: 10.1039/c5dt03991f. View

19.

Solomon R, Bella A, Vedha S, Venuvanalingam P . Designing benzosiloles for better optoelectronic properties using DFT & TDDFT approaches. Phys Chem Chem Phys. 2012; 14(41):14229-37. DOI: 10.1039/c2cp41554b. View

20.

Ando N, Mitsui M, Nakajima A . Photoelectron spectroscopy of cluster anions of naphthalene and related aromatic hydrocarbons. J Chem Phys. 2008; 128(15):154318. DOI: 10.1063/1.2903473. View