Novel pH-Independent Amphiphilic Chlorophyll a Derivatives with Oligoethyleneglycol Substituents as a Hydrophilic Part: Synthesis and Hydrophilicity Estimation

Belykh D.V.,^@ Startseva O.M., Patov S.A.

Institute of Chemistry, Komi Scientifi c Center, Ural Division, Russian Academy of Sciences, Pervomaiskaya st. 48, Syktyvkar 167982, Russia.

^@Corresponding author E-mail: belykh-dv@chemi.komisc.ru, belykh-dv@mail.ru

DOI: 10.6060/mhc140500b

Macroheterocycles 2014 7(4) 401-413

Several novel pH-independent amphiphilic chlorophyll a derivatives with oligoethylene glycol substituent’s as a hydrophilic part were synthesized and hydrophilicity estimation was carried out using their mobility on reverse phase gel HPLC data. The oligoethylene glycol substituent insertion has been shown to increases the hydrophilicity of the whole molecule significantly. The most important structural factors affected hydrophylicity are the presence or absence of the exocycle (exocycle opening results in hydrophobicity decrease in case of the same length oligoethylene glycol chain), and the position of the oligoethylene glycol substituent (the more length of the spacer between the macrocycle and oligoethylene glycol substituent’s the higher hydrophilicity is). Oligoetylene glycol chain elongation does not lead to an appreciable increase in hydrophilicity. So more affordable di-, tri- and tetraethylene glycols may be used for chlorophyll a derivatives hydrophilization instead of the less available penta-and hexamers.

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Novel pH-Independent Amphiphilic Chlorophyll a Derivatives with Oligoethyleneglycol Substituents as a Hydrophilic Part: Synthesis and Hydrophilicity Estimation

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