Photoluminescence and Quantum Yields of Urea and
Urethane Cross-Linked Nanohybrids Derived from
Carboxylic Acid Solvolysis
Lianshe Fu, R. A. Sa ´ Ferreira, N. J. O. Silva, and L. D. Carlos*
Departamento de Fı ´sica, CICECO, Universidade de Aveiro, 3810-193 Aveiro, Portugal
V. de Zea Bermudez
Departamento de Quı ´mica and CQ-VR, Universidade de Tra ´ s-os-Montes e Alto Douro,
5000-911 Vila Real Codex, Portugal
J. Rocha
Departamento de Quı ´mica, CICECO, Universidade de Aveiro, 3810-193 Aveiro, Portugal
Received October 17, 2003. Revised Manuscript Received February 6, 2004
Urea and urethane cross-linked hybrids, classed as di-ureasils and di-urethanesils, were
prepared through sol-gel derived carboxylic acid solvolysis. The resulting nanohybrids were
characterized by X-ray diffraction, mid-infrared spectroscopy,
29
Si and
13
C nuclear magnetic
resonance, and photoluminescence spectroscopy and results were compared with those of
similar hybrid materials obtained from the conventional sol-gel route. The results indicate
a similar structure for the hybrids, independent of the synthesis process used. All the hybrids
are efficient room-temperature white-light emitters with emission quantum yields between
6 and 20%. The emission quantum yields of hybrids prepared through carboxylic acid
solvolysis are 27-35% higher than those calculated for the di-ureasils and di-urethanesils
synthesized via the conventional sol-gel technique. This is attributed to the presence of a
larger number of nonbonded NH urea- and urethane-groups in the hybrids prepared by
carboxylic acid solvolysis, illustrating the key role played by the synthetic method on the
extent and magnitude of hydrogen bonding involving urea and urethane linkages.
I. Introduction
In the last two decades, the drive to miniaturization
has been pushing industry into the atomic and nanom-
eter scales requiring the development of new strategies
for the synthesis of advanced materials. Among the
available synthetic methods employed for the develop-
ment of nanosystems, the sol-gel procedure presents
advantages such as relatively low processing tempera-
ture, high purity, improvement of the thermal and di-
mensional stability of the resulting compounds, and ease
of shaping the product into thin films, fibers, and
monoliths.
1,2
Pure and well-controlled multifunctional
organic-inorganic hybrids may be synthesized through
a molecular nanotechnology “bottom-up” approach based
on a tailored assembly of nanoscopic organic and inor-
ganic building blocks. This opens up exciting new
avenues in materials science and related technologies
with significant implications in nanotechnological pro-
cessing, which facilitate integration, miniaturization,
and multifunctionalization of devices.
3-12
In particular,
the sol-gel approach offers the flexibility necessary
for implementing the chemical design strategies that
are the basis of photonic hybrid materials, one of the
most attractive fields for applications in the 21st
century.
7,8,13-15
The outgrowth of new full color displays that are
cheaper and less aggressive to the global environment
is one of the main challenging tasks for the next gen-
eration of flat-panel display systems and lighting tech-
nology. The hybrid concept has been recently employed
to synthesize stable and efficient full-color luminescent
siloxane-based organic-inorganic materials lacking metal
activator ions.
16-28
Emphasis is given to amide- or
* Corresponding author. Phone: 351 234 370946. Fax: 351 234
424965. E-mail: lcarlos@fis.ua.pt.
(1) Hench, L. L.; West, J. K. Chem. Rev. 1990, 90, 33.
(2) Brinker, C. J.; Scherer, G. W. Sol-gel Science: The Physics and
Chemistry of Sol-Gel Processing; Academic: San Diego, CA, 1990.
(3) Novak, B. M. Adv. Mater. 1993, 5, 422.
(4) Sanchez, C.; Ribot, F. New J. Chem. 1994, 18, 1007.
(5) Schubert, U.; Hu ¨ sing, N.; Lorenz, A. Chem. Mater. 1995, 7, 2010.
(6) Loy, D. A.; Shea, K. J. Chem. Rev. 1995, 95, 1431.
(7) Judeinstein, P.; Sanchez, C. J. Mater. Chem. 1996, 6, 511.
(8) Wen, J. Y.; Wilkes, G. L. Chem. Mater. 1996, 8, 1667.
(9) Sanchez, C.; Ribot, F.; Lebeau, B. J. Mater. Chem. 1999, 9, 35.
(10) Ahmad, Z.; Mark, J. E. Chem. Mater. 2001, 13, 3320.
(11) Mitzi, D. B. Chem. Mater. 2001, 13, 3283.
(12) Ben, F.; Boury, B.; Corriu, R. J. P. Adv. Mater. 2002, 14, 1081.
(13) Schmidt, H.; Jonschker, G.; Goedicke, S.; Mennig, M. J. Sol-
Gel Sci. Technol. 2000, 19, 39.
(14) Sanchez, C.; Lebeau, B. In Hybrid Organic-Inorganic Materi-
als; Loy, D. A., Ed.; Mater. Res. Soc. Bull. 2001, 26, 377.
(15) Scott, B. J.; Wirnsberger, G.; Stucky, G. D. Chem. Mater. 2001,
13, 3140.
(16) Green, W. H.; Le, K. P.; Grey, J.; Au, T. T.; Sail, M. J. Science
1997, 276, 1826.
(17) (a) Bekiari, V.; Lianos, P. Langmuir 1998, 14, 3459. (b) Bekiari,
V.; Lianos, P. Chem. Mater. 1998, 10, 3777.
1507 Chem. Mater. 2004, 16, 1507-1516
10.1021/cm035028z CCC: $27.50 © 2004 American Chemical Society
Published on Web 03/19/2004