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Volumn 107, Issue 21, 2003, Pages 4203-4210

Ground- and excited-state proton transfer in anthocyanins: From weak acids to superphotoacids

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; FLUORESCENCE; GROUND STATE; LASER APPLICATIONS; PH EFFECTS; PHOTOLYSIS; PHOTONS; PROTONS; RATE CONSTANTS; WATER;

EID: 0037863874     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp027260i     Document Type: Article
Times cited : (54)

References (38)
  • 2
    • 0038790259 scopus 로고
    • Markakis, P., Ed.; Academic Press: New York; Chapter 9
    • Brouillard, R. In Anthocyanins as Food Colors; Markakis, P., Ed.; Academic Press: New York, 1982; Chapter 9.
    • (1982) Anthocyanins As Food Colors
    • Brouillard, R.1
  • 21
    • 0038113230 scopus 로고    scopus 로고
    • Ph.D. Thesis, Instituto Superior Técnico, Lisbon, Portugal
    • Lima, J. C. Ph.D. Thesis, Instituto Superior Técnico, Lisbon, Portugal, 1996.
    • (1996)
    • Lima, J.C.1
  • 24
    • 0038452583 scopus 로고    scopus 로고
    • release 6.01 for Windows; Hypercube, Inc.: Gainesville, FL
    • Hyperchem, release 6.01 for Windows; Hypercube, Inc.: Gainesville, FL, 2000.
    • (2000) Hyperchem
  • 34
    • 0038452586 scopus 로고    scopus 로고
    • note
    • Although the participation of preformed ground-state hydrogen-bonded complexes, in which water molecules are in an appropriate position for receiving the proton from the anthocyanin, cannot be excluded, intramolecular proton-transfer rates are known to exceed the 6-7 ps limit. The fact that these compounds are almost exclusively soluble in water or aqueous ethanol or methanol mixtures limits the use of solvatochromic studies to resolve this point. Nonetheless, preliminary results on the solvatochromism of the synthetic anthocyanin 7-hydroxy-4-methylflavylium (HMF) chloride have shown that the solvent-induced stabilization of the ground state (blue shift of the absorption spectrum) of HMF is proportional to the hydrogen bond donating ability of the solvent while the stabilization of the excited state (red shift of the emission spectrum) is correlated with the hydrogen bond accepting capacity of the solvent. This suggests the presence of hydrogen-bonded HMF-water complexes in both the ground and excited states. However, in the ground state, water molecules are predominantly hydrogen-bond donors to HMF, whereas in the excited state water acts predominantly as a hydrogen-bond acceptor. Thus, excitation would require rotational relaxation of the water molecules in the solvation shell of HMF prior to proton transfer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.