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Design and Development of a New Pyrromethene Dye with Improved Photostability and Lasing Efficiency: Theoretical Rationalization of Photophysical and Photochemical Properties

Supporting Info

Soumyaditya Mula,^† Alok K. Ray,^‡ Manas Banerjee,^§ Tandrima Chaudhuri,^§ Kamalesh Dasgupta,^‡ and Subrata Chattopadhyay*^†

Bio-Organic Division, Laser and Plasma Technology Division, Bhabha Atomic Research Centre, Mumbai - 400085, India, and Chemistry Department, Burdwan University, Burdwan - 713104, India

J. Org. Chem., 2008, 73 (6), pp 2146–2154

DOI: 10.1021/jo702346s

Publication Date (Web): February 27, 2008

†

Bio-Organic Division, Bhabha Atomic Research Centre.

‡

Laser and Plasma Technology Division, Bhabha Atomic Research Centre.

Burdwan University.

Fax: 91-22-5505151.

, schatt@barc.gov.in

Abstract

In an attempt to develop a photostable and efficient pyrromethene compound for use in liquid dye lasers, three congeners of the commercially available pyrromethene 567 (PM567) laser dye were synthesized and their photophysical properties, lasing efficiencies, and photochemical stabilities were studied. In general the presence of an aryl group at C-8 of the pyrromethene chromophore increased the photostability. One of the congeners possessing a C-8 trimethoxyphenyl moiety showed significantly improved lasing parameters than PM567. Compared to PM567, the photochemical stability of the new dye was 2-fold, while it showed an equivalent lasing efficiency to that of PM567 at a significantly lower concentration. The increased photostability of these new dye molecules could be explained by theoretical calculation on their capacity to generate singlet oxygen (¹O₂) and probability of reaction with ¹O₂. Our calculations were in agreement with the experimental results and indicated that a systematic design of new derivatives of pyrromethene chromophore might lead to improved laser dye molecules.

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