Monoisomeric Phthalocyanines and Phthalocyanine–Fullerene Dyads with Polar Side Chains: Synthesis, Modeling, and Photovoltage

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• 作者：Jenni Ranta ; Kimmo Kaunisto ; Mika Niskanen ; Alexander Efimov ; Terttu I. Hukka ; Helge Lemmetyinen
• 刊名：Journal of Physical Chemistry C
• 出版年：2014
• 出版时间：February 6, 2014
• 年：2014
• 卷：118
• 期：5
• 页码：2754-2765
• 全文大小：545K
• ISSN：1932-7455

文摘

Synthesis, characterization, molecular modeling, and photovoltage responses of four phthalocyanine鈥揻ullerene (Pc-C₆₀) dyads with two polar (鈭扥H) side chains are described. The synthesized dyads have polar tails either on the Pc (electron donor D) side or on the fullerene (electron acceptor A) side of the dyad, providing a possibility to produce oriented donor鈥揳cceptor (D鈥揂) monolayers with revised electron transfer direction when deposited on an aqueous subphase or on a solid surface. In the dyads, phthalocyanine and fullerene have different mutual orientations: in the trans-dyads they have face-to-face orientation, while in the cis-dyads the orientation is face-to-edge. Molecular modeling was used to examine and confirm the spatial arrangements of the synthesized dyads. The Pc-C₆₀ dyads were deposited successfully onto solid substrates as highly oriented monolayers using the Langmuir鈥揝ch盲fer method. Formation of a vertically oriented monolayer and the following electron transfer from the photoexcited phthalocyanine to fullerene was demonstrated for all dyad monolayers by the time-resolved Maxwell displacement charge method. The electron transfer direction was reversed for the dyads with reversed polarity, demonstrating the ability to control charge transfer direction in the film.