Self-assembly of Photofunctional Siloxane-Based Calix[4]arenes on Oxide Surfaces

Tamar Van der Boom, Guennadi Evmenenko, Pulak Dutta, Michael R Wasielewski

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

The synthesis of photofunctional calix[4]arenes and the formation and characterization of self-assembled monolayers (SAMs) made from them is described. Two identical 4-(N-piperidinyl)naphthalene-1,8-dicarboximide or perylene-3,4:9,10-bis(dicarboximide) chromophores were covalently attached to the upper rim of calix[4]arene at the 1- and 3-positions, whereas the lower rim was functionalized with four reactive silane groups to ensure strong, covalent multisite binding to hydrophilic oxide surfaces such as quartz and silicon wafers. This strategy allows spatially proximate chromophoric dimers to be attached to surfaces, while offering the flexibility of isolating or diluting these dimer units on the surface. Homo- and heterogeneous nanoscale thin films (1.2-2.1-nm thick) were assembled from solution and characterized using synchrotron X-ray specular reflectivity, advancing contact angle measurements, atomic force microscopy, and optical absorption and fluorescence spectroscopy. Optical spectroscopy of the films show that strong electronic interactions occur between the perylene-3,4:9,10-bis(dicarboximide) dimers, while the 4-(N-piperidinyl)naphthalene-1,8-dicarboximide dimers show little interaction. However, in the latter case, the solvatochromic nature of the chromophore illustrates the low-polarity environment of the films.

Original languageEnglish
Pages (from-to)4068-4074
Number of pages7
JournalChemistry of Materials
Volume15
Issue number21
DOIs
Publication statusPublished - Oct 21 2003

Fingerprint

Siloxanes
Dimers
Self assembly
Oxides
Perylene
Naphthalene
Chromophores
Silanes
Quartz
Fluorescence spectroscopy
Self assembled monolayers
Angle measurement
Synchrotrons
Silicon wafers
Absorption spectroscopy
Light absorption
Contact angle
Atomic force microscopy
X rays
Thin films

ASJC Scopus subject areas

  • Materials Chemistry
  • Materials Science(all)

Cite this

Self-assembly of Photofunctional Siloxane-Based Calix[4]arenes on Oxide Surfaces. / Van der Boom, Tamar; Evmenenko, Guennadi; Dutta, Pulak; Wasielewski, Michael R.

In: Chemistry of Materials, Vol. 15, No. 21, 21.10.2003, p. 4068-4074.

Research output: Contribution to journalArticle

Van der Boom, Tamar ; Evmenenko, Guennadi ; Dutta, Pulak ; Wasielewski, Michael R. / Self-assembly of Photofunctional Siloxane-Based Calix[4]arenes on Oxide Surfaces. In: Chemistry of Materials. 2003 ; Vol. 15, No. 21. pp. 4068-4074.
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