Study of Model Systems for Bilirubin and Bilin Chromophores: Determination and Modification of Thermal and Photochemical Properties

  1. García-Iriepa, C. 3
  2. Ernst, H.A. 2
  3. Liang, Y. 2
  4. Unterreiner, A.-N. 2
  5. Frutos, L.M. 3
  6. Sampedro, D. 1
  1. 1 Universidad de La Rioja

    Universidad de La Rioja

    Logroño, España


  2. 2 Karlsruhe Institute of Technology

    Karlsruhe Institute of Technology

    Karlsruhe, Alemania


  3. 3 Universidad de Alcalá

    Universidad de Alcalá

    Alcalá de Henares, España


Journal of Organic Chemistry

ISSN: 0022-3263

Year of publication: 2016

Volume: 81

Issue: 15

Pages: 6292-6302

Type: Article

DOI: 10.1021/ACS.JOC.6B00892 SCOPUS: 2-s2.0-84981203572 WoS: WOS:000381236000015 GOOGLE SCHOLAR

More publications in: Journal of Organic Chemistry


Cited by

  • Scopus Cited by: 10 (08-03-2023)
  • Web of Science Cited by: 4 (28-03-2023)

JCR (Journal Impact Factor)

  • Year 2016
  • Journal Impact Factor: 4.849
  • Journal Impact Factor without self cites: 4.335
  • Article influence score: 1.058
  • Best Quartile: Q1
  • Area: CHEMISTRY, ORGANIC Quartile: Q1 Rank in area: 8/59 (Ranking edition: SCIE)

SCImago Journal Rank

  • Year 2016
  • SJR Journal Impact: 2.001
  • Best Quartile: Q1
  • Area: Organic Chemistry Quartile: Q1 Rank in area: 14/192

Scopus CiteScore

  • Year 2016
  • CiteScore of the Journal : 8.3
  • Area: Organic Chemistry Percentile: 92


Bilin chromophores and bilirubin are involved in relevant biological functions such as light perception in plants and as protective agents against Alzheimer and other diseases. Despite their extensive use, a deep rationalization of the main factors controlling the thermal and photochemical properties has not been performed yet, which in turn hampers further applications of these versatile molecules. In an effort to understand those factors and allow control of the relevant properties, a combined experimental and computational study has been carried out for diverse model systems to understand the interconversion between Z and E isomers. In this study, we have demonstrated the crucial role of steric hindrance and hydrogen-bond interactions in thermal stability and the ability to control them by designing novel compounds. We also determined several photochemical properties and studied the photodynamics of two model systems in more detail, observing a fast relaxation of the excited state shorter than 2 ps in both cases. Finally, the computational study allowed us to rationalize the experimental evidence. © 2016 American Chemical Society.