Fullerene-indene adducts (ICMA & ICBA) in an astrochemical perspective part 1: chemical thermodynamics, stability and electronic absorption spectroscopy

References

• Burkhardt, A. M.; Long Kelvin Lee, K.; Bryan Changala, P.; Shingledecker, C. N.; Cooke, I. R.; Loomis, R. A.; Wei, H.; Charnley, S. B.; Herbst, E.; McCarthy, M. C.; McGuire, B. A. Discovery of the Pure Polycyclic Aromatic Hydrocarbon Indene (c-C9H8) with GOTHAM Observations of TMC-1. ApJL 2021, 913, L18. DOI: 10.3847/2041-8213/abfd3a.]
   Web of Science ®Google Scholar
• Cernicharo, J.; Agúndez, M.; Cabezas, C.; Tercero, B.; Marcelino, N.; Pardo, J. R.; de Vicente, P. Pure Hydrocarbon Cycles in TMC-1: Discovery of Ethynyl Cyclopropenylidene, Cyclopentadiene, and Indene. A&A 2021, 649, L15. DOI: 10.1051/0004-6361/202141156.
   PubMed Web of Science ®Google Scholar
• Doddipatla, S.; Galimova, G. R.; Wei, H.; Thomas, A. M.; He, C.; Yang, Z.; Morozov, A. N.; Shingledecker, C. N.; Mebel, A. M.; Kaiser, R. I. Low-Temperature Gas-Phase Formation of Indene in the Interstellar Medium. Sci. Adv. 2021, 7, eabd4044. DOI: 10.1126/sciadv.abd4044.
   PubMed Web of Science ®Google Scholar
• (a) Goeres, A.; Sedlmayr, E. On the Nucleation Mechanism of Effective Fullerite Condensation. Chem. Phys. Lett. 1991, 184, 310–317. 10.1016/0009-2614(91)85129-K
   Web of Science ®Google Scholar
  (b) Broyer, M.; Goeres, A.; Pellarin, M.; Sedlmayr, E.; Louis Vialle, J.; Wöste, L. Experimental Studies on the Formation Process of C60. Chem. Phys. Lett. 1992, 198, 128–134. 10.1016/0009-2614(92)90060-Z
   Web of Science ®Google Scholar
  (c) Goeres, A.; Sedlmayr, E. Hydrogen-Blocking in C60-Formation Theories. Fullerenes Nanot. Carbon Nanostruct.1993, 1, 563–570. DOI: 10.1080/15363839308009532.
   Google Scholar
• Scott, A.; Duley, W. W.; Pinho, G. P. Polycyclic Aromatic Hydrocarbons and Fullerenes as Decomposition Products of Hydrogenated Amorphous Carbon. Astrophys. J 1997, 489, L193–L195. DOI DOI: 10.1086/316789.
   Web of Science ®Google Scholar
• García-Hernández, D. A.; Villaver, E.; García-Lario, P.; Acosta-Pulido, J. A.; Manchado, A.; Stanghellini, L.; Shaw, R. A.; Cataldo, F. Infrared Study of Fullerene Planetary Nebulae. ApJ 2012, 760, 107. DOI DOI: 10.1088/0004-637X/760/2/107.
   Web of Science ®Google Scholar
• Gielen, C.; Cami, J.; Bouwman, J.; Peeters, E.; Min, M. Carbonaceous Molecules in the Oxygen-Rich Circumstellar Environment of Binary post-AGB stars-C60 Fullerenes and Polycyclic Aromatic Hydrocarbons. A&A 2011, 536, A54. DOI: 10.1051/0004-6361/201117961.
   Web of Science ®Google Scholar
• García-Hernández, D. A.; Manchado, A.; García-Lario, P.; Stanghellini, L.; Villaver, E.; Shaw, R. A.; Szczerba, R.; Perea-Calderón, J. V. Formation of Fullerenes in H-Containing Planetary Nebulae. ApJ 2010, 724, L39–L43. DOI DOI: 10.1088/2041-8205/724/1/L39.
   Web of Science ®Google Scholar
• (a) Garcia-Hernandez, D. A.; Cataldo, F.; Manchado, A. Charge-Transfer Interaction between C60 Fullerene and Alkylnaphthalenes. Fullerenes Nanot. Carbon Nanostruct. 2017, 25, 223–229.
   Web of Science ®Google Scholar
  (b) García-Hernández, D. A.; Cataldo, F.; Manchado, A. C70 Fullerene Charge-Transfer Interaction with Alkylnaphthalenes, Pinenes, and a Diene. Fullerenes Nanot. Carbon Nanostruct. 2017, 25, 505–511. 10.1080/1536383X.2017.1329202 DOI: 10.1080/1536383X.2016.1277993.
   Web of Science ®Google Scholar
• (a) García-Hernández, D. A.; Cataldo, F.; Manchado, A. Infrared Spectroscopy of Fullerene C60/Anthracene Adducts. Monthly Notices Royal Astronom. Soc. 2013, 434, 415–422.
   Web of Science ®Google Scholar
  (b) Cataldo, F.; García-Hernández, D. A.; Manchado, A. Sonochemical Synthesis of Fullerene C60/Anthracene Diels-Alder Mono and Bis-Adducts. Fullerenes Nanot. Carbon Nanostruct. 2014, 22, 565–574. 10.1080/1536383X.2012.702160 DOI: 10.1093/mnras/stt1032.
   Web of Science ®Google Scholar
• Zhen, J.; Zhang, W.; Yang, Y.; Zhu, Q.; Tielens, A. G. G. M. Laboratory Formation and Photochemistry of Fullerene/Anthracene Cluster Cations. ApJ 2019, 887, 70. DOI DOI: 10.3847/1538-4357/ab4f73.
   Web of Science ®Google Scholar
• Cataldo, F.; García-Hernández, D. A.; Manchado, A. A Study on the Synthesis and Stability of the C60 Fullerene/Tetracene Adduct. Eur. Chem. Bull 2014, 3, 740–744.
   Google Scholar
• Cataldo, F.; García-Hernández, D. A.; Manchado, A. On the C60 Fullerene Adduct with Pentacene: Synthesis and Stability. Fullerenes Nanot. Carbon Nanostruct 2015, 23, 818–823. DOI: 10.1080/1536383X.2015.1006398.
   Web of Science ®Google Scholar
• Garcia-Hernandez, D. A.; Cataldo, F.; Manchado, A. Acenes Adducts with C70 Fullerene: Anthracene, Tetracene and Pentacene. Fullerenes Nanot. Carbon Nanostruct 2016, 24, 679–687. DOI: 10.1080/1536383X.2016.1216987.
   Web of Science ®Google Scholar
• Cataldo, F.; García-Hernández, D. A.; Manchado, A. Chemical Thermodynamics Applied to the Diels–Alder Reaction of C60 Fullerene with Polyacenes. Fullerenes Nanot. Carbon Nanostruct 2015, 23, 760–768. DOI: 10.1080/1536383X.2014.997354.
   Web of Science ®Google Scholar
• Sabirov, D. S.; Terentyev, A. O.; Cataldo, F. Bisadducts of the C60 and C70 Fullerenes with Anthracene: Isomerism and DFT Estimation of Stability and Polarizability. Computat. Theor. Chem 2016, 1081, 44–48. DOI: 10.1016/j.comptc.2016.02.012.
   Web of Science ®Google Scholar
• Rodrigues, D. J.; Santos, L. M.; Melo, A.; Lima, C. F. Theoretical Study on the Diels–Alder Reaction of Fullerenes: Analysis of Isomerism, Aromaticity, and Solvation. Organics 2022, 3, 364–379. DOI: 10.3390/org3040025.
   Google Scholar
• Puplovskis, A.; Kacens, J.; Neilands, O. New Route for [60] Fullerene Functionalisation in [4 + 2] Cycloaddition Reaction Using Indene. Tetrahedron Lett 1997, 38, 285–288. (96)02293-9 DOI: 10.1016/S0040-4039.
   Web of Science ®Google Scholar
• Dean, J. A. Lange’s Handbook of Chemistry, 15th ed. McGraw-Hill: New York, 1999.
   Google Scholar
• (a) Wannere, C. S.; Moran, D.; Allinger, N. L.; Hess, B. A.; Schaad, L. J.; Schleyer, P. V. R. On the Stability of Large [4n] Annulenes.Org Lett. 2003, 5, 2983–2986. 10.1021/ol034979f
   PubMed Web of Science ®Google Scholar
  (b) McCullogh, J.J. Xylylenes and Isoindenes as Reaction Intermediates. Acc. Chem. Res. 1980, 13, 270–276. DOI: 10.1021/ar50152a004.
   Web of Science ®Google Scholar
• Barham, J. P.; Tanaka, S.; Koyama, E.; Ohneda, N.; Okamoto, T.; Odajima, H.; Sugiyama, J.-I.; Norikane, Y. ;. Selective, Scalable Synthesis of C60-Fullerene/Indene Monoadducts Using a Microwave Flow Applicator. J Org Chem 2018, 83, 4348–4354. DOI: 10.1021/acs.joc.7b03209.
   PubMed Web of Science ®Google Scholar
• Zhao, G.; He, Y.; Li, Y. Indene − C60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells. Adv Mater 2010, 22, 4355–4358. DOI: 10.1021/ja908602j.
   PubMed Web of Science ®Google Scholar
• Yamane, S.; Mizukado, J.; Uchimaru, T.; Suzuki, Y.; Chen, L.; Suda, H. Photooxidation Studies on indene-C60 Adducts. Solar Ener. Mater. Solar Cells 2015, 143, 135–140. DOI: 10.1016/j.solmat.2015.06.045.
   Web of Science ®Google Scholar
• (a) Benson, S. W. Thermochemical Kinetics. Methods for Estimation of Thermochemical Data and Rate Parameters. J. Wiley & Sons: New York, 1968.
   Google Scholar
  (b) Cohen, N.; Benson, S. W. Estimation of Heats of Formation of Organic Compounds by Additivity Methods. Chem. Rev 1993, 93, 2419–2438. DOI: 10.1021/cr00023a005.
   Google Scholar
• Van Krevelen, D. W. Properties of Polymers: Their Estimation and Correlation with Chemical Structure, 3rd ed.; Elsevier: Amsterdam, 1990, Chapter20
   Google Scholar
• Cataldo, F.; Barzaga, R.; García-Hernández, D. A.; Manchado, A. Thermochemical Properties of C60Br24. Fullerenes Nanot. Carbon Nanostruct 2023, 31, 505–512. published online March 9, 2023. DOI DOI: 10.1080/1536383X.2023.2187049.
   Web of Science ®Google Scholar
• Cataldo, F.; Barzaga, R.; García-Hernández, D. A.; Arenal, R.; Manchado, A. Synthesis of a New Cyanofullerene Derivative. Fullerenes Nanot. Carbon Nanostruct 2023, 31, 505–512. DOI: 10.1080/1536383X.2023.2199988.
   Web of Science ®Google Scholar
• NIST Chemistry WebBook consulted 11/04/2023: https://webbook.nist.gov/cgi/cbook.cgi?ID=C99685968&Units=SI&Mask=2#Thermo-Condensed.
   Google Scholar
• Rodrigues, D. J. L., 2022. Kinetics and Thermodynamics of the Diels-Alder Addition to Fullerenes. Thesis, Faculdade de Ciências da Universidade do Porto, Portugal. Relator: Costa Lima, C.F.R.A; Co-relator: das Neves Belchior Faia dos Santos, L.M
   Google Scholar
• Cataldo, F.; Kanazirev, V. Synthesis and Thermal Stability of Mercury Diacetylide Hg(C≡CH)2. Polyhedron 2013, 62, 42–50. DOI: 10.1016/j.poly.2013.06.005.
   Web of Science ®Google Scholar
• Cataldo, F.; Ursini, O.; Angelini, G. and Explosive Decomposition of Polynitro[60] Fullerene. Carbon 2013, 62, 413–421. DOI: 10.1016/j.carbon.2013.06.026.
   Web of Science ®Google Scholar
• Cataldo, F.; Iglesias-Groth, S. A. Differential Scanning Calorimetric (DSC) Study on Heavy Ozonized C60 Fullerene. Fullerenes Nanot. Carbon Nanostruct 2015, 23, 253–258. DOI: 10.1080/1536383X.2014.905771.
   Web of Science ®Google Scholar
• Cataldo, F.; Hafez, Y.; Iglesias-Groth, S. Thermal Decomposition of Ozonized C70 Fullerene and Its Reducing Properties toward Silver Ions. Fullerenes Nanot. Carbon Nanostruct 2015, 23, 1037–1042. DOI: 10.1080/1536383X.2015.1057574.
   Web of Science ®Google Scholar
• Cataldo, F. Thermal Stability, Decomposition Enthalpy, and Raman Spectroscopy of 1-Alkene Secondary Ozonides. Tetrahedron Lett 2015, 56, 994–998. DOI: 10.1016/j.tetlet.2015.01.056.
   Web of Science ®Google Scholar
• Cataldo, F. Thermochemistry of Sulfur-Based Vulcanization and of Devulcanized and Recycled Natural Rubber Compounds. IJMS 2023, 24, 2623. DOI: 10.3390/ijms24032623.
   Google Scholar
• Höhne, G.; McNaughton, J. L.; Hemminger, W.; Flammersheim, H. J.; Flammersheim, H. J. Differential Scanning Calorimetry. Springer Science: Berlin, 2003.
   Google Scholar
• Koga, N.; Vyazovkin, S.; Burnham, A. K.; Favergeon, L.; Muravyev, N. V.; Perez-Maqueda, L. A.; Saggese, C.; Sánchez-Jiménez, P. E. ICTAC Kinetics Committee Recommendations for Analysis of Thermal Decomposition Kinetics. Thermochim. Acta 2023, 719, 179384–179333. pages DOI: 10.1016/j.tca.2022.179384.
   Web of Science ®Google Scholar
• Leach, S.; Vervloet, M.; Desprès, A.; Bréheret, E.; Hare, J. P.; John Dennis, T.; Kroto, H. W.; Taylor, R.; Walton, D. R. ;. Electronic Spectra and Transitions of the Fullerene C60. Chem. Phys 1992, 160, 451–466. DOI: 10.1016/0301-0104(92)80012-K.
   Web of Science ®Google Scholar
• Cataldo, F.; Iglesias-Groth, S.; Hafez, Y. On the Molar Extinction Coefficients of the Electronic Absorption Spectra of C60 and C70 Fullerenes Radical Cation. Eur. Chem. Bull 2013, 2, 1013–1018.
   Google Scholar