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Publication Title | Introduction to Synthetic Organic Photochemistry

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Flow Photochemistry – a Green Technology with a Bright Future

Michael Oelgemöller, Tyler Goodine, and Padmakana Malakar

1.1 Introduction to Synthetic Organic Photochemistry

According to the International Union of Pure and Applied Chemistry (IUPAC), photochemistry is “the branch of chemistry concerned with the chemical effects of ultraviolet, visible, or infrared radiation” [1]. Owing to the multidisciplinary nature of light, photochemistry thus finds widespread applications in the fields of analytical, environmental, food, inorganic, material, medicinal, organic, phar- maceutical, polymer, and physical chemistry [2, 3]. In terms of organic synthesis, light energy is utilized to activate molecules within their chromophoric groups. For multichromophoric substrates, this activation can be selectively achieved [4]. e amount of energy required for activation corresponds to the wavelength of the light as expressed in the Planck relation (Equation 1.1) [5]:

E = h × v = h × c ∕ 𝜆 = h × c × 𝜐̃ ( 1 . 1 )

where E is the energy of light; h, the Planck constant; v, the frequency; c, the velocity of light; 𝜆, the wavelength; and 𝜐̃, the wavenumber.

e excited state reached can undergo a multitude of energy- as well as electron-transfer processes, which are commonly shown in a Jablonski diagram [6]. Deactivation processes are common and include fluorescence, phospho- rescence, or internal conversion. Alternatively, the excited state energy can be utilized for chemical changes. Owing to the different structural and physic- ochemical properties of excited states, photochemical reactions can differ significantly from thermal reactions. ere are three main photochemical pro- cesses (Scheme 1.1) [1]: direct excitation, photosensitization, and photoinduced electron transfer reactions. In the first case, light is absorbed by the substrate and its subsequent excited state can undergo a chemical transformation either on its own or by reaction with another (ground-state) molecule. In the second case, light energy is used to activate a photosensitizer (or photocatalyst) into its excited state. is excess of energy is consequently transferred to another substrate by collision. e latter reagent enters its corresponding excited state and can undergo further chemical changes. In the third reaction mode, an electron is transferred between the excited state of one compound and the ground state of another substrate. e corresponding radical-ion pair can

Sustainable Flow Chemistry: Methods and Applications, First Edition. Edited by Luigi Vaccaro.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2017 by Wiley-VCH Verlag GmbH & Co. KGaA.


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