Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped chalconyl substituted organotriethoxysilanes

Article abstract of DOI:10.1016/j.jorganchem.2014.11.022

Organotriethoxysilanes (OTES) play an impressive role in the designing of organic-inorganic hybrid materials. The highly efficient copper catalysed 'Click Silylation' is followed for the functionalization of 3-azidopropyltriethoxysilane (AzPTES) with a se

Full text of DOI:10.1016/j.jorganchem.2014.11.022

Accepted Manuscript
Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped
chalconyl substituted organotriethoxysilanes
Dr. Gurjaspreet Singh , Assistant Professor, Aanchal Arora , Satinderpal Singh
Mangat , Jandeep Singh , Sunita Rani , Navneet Kaur
PII:
S0022-328X(14)00581-6
10.1016/j.jorganchem.2014.11.022
JOM 18816
DOI:
Reference:
To appear in: Journal of Organometallic Chemistry
Received Date: 25 September 2014
Revised Date: 14 November 2014
Accepted Date: 20 November 2014
Please cite this article as: G. Singh, A. Arora, S.S. Mangat, J. Singh, S. Rani, N. Kaur,
Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped chalconyl
substituted organotriethoxysilanes, Journal of Organometallic Chemistry (2014), doi: 10.1016/
j.jorganchem.2014.11.022.
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Graphical Abstract (Synopsis)
Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped chalconyl
substituted organotriethoxysilanes
Gurjaspreet Singha,*, Aanchal Aroraa, Satinderpal Singh Mangata, Jandeep Singha, Sunita Rania,
Navneet Kaurb
Chalconyl blended triazole allied organotriethoxysilanes (8a-8u) were synthesized from
1
acetylinic chalcones (7a-7u) and fully characterized by IR, H and 13C NMR spectroscopy.
Highly potential ‘Click silylation’ route is followed for the synthesis. The photo-physical
properties of all the synthesized silanes were compared on the basis of different substitutions.

ACCEPTED MANUSCRIPT
Graphical Abstract

ACCEPTED MANUSCRIPT
Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped
chalconyl substituted organotriethoxysilanes
Gurjaspreet Singha*, Aanchal Aroraa, Satinderpal Singh Mangata, Jandeep Singha, Sunita
Rania, Navneet Kaurb
aDepartment of Chemistry and Centre of Advanced Studies, Panjab University, Chandigarh,
160014, India
bCentre for Nano-science and Nano-technology, Panjab University, Chandigarh, 160014,
India
*Corresponding Author
Dr. Gurjaspreet Singh
Assistant Professor
Department of Chemistry and Centre of Advanced Studies
P.U., Chandigarh
India
+91-0172-2534428, +91-1881-242176
Email: gjpsingh@pu.ac.in
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Synthetic investigations and photo-physical properties of 1,2,3-triazole encapped
chalconyl substituted organotriethoxysilanes
Abstract
Organotriethoxysilanes (OTES) play an impressive role in the designing of organic-inorganic
hybrid materials. The highly efficient copper catalyzed ‘Click Silylation’ is followed for the
functionalization of 3-azidopropyltriethoxysilane (AzPTES) with a series of acetylinic
chalcones. Chalcones being ubiquitous subunits present in various natural products possess a
wide variety of biological activities and are thus considered for the synthesis of new hybrid
templates. Twenty one new chalcone holding triazole encapped OTES were synthesized in
quantitative yields. All the synthesized compounds were well characterized by IR, 1H and 13C
NMR spectroscopic techniques. The photo-physical properties of all the OTES were
compared and the effect of different substitutions was explicated. These OTES can be put to
amazing applications in the field of medicine and material chemistry.
Keywords: Click Silylation, Organotriethoxysilanes, 1,2,3-Triazole, Chalcones
1. Introduction
Organotriethoxysilanes (OTES) are promising materials for applications in diverse fields
such as drug delivery, catalysis, enzyme immobilization, optics, polymer chemistry and
chemical sensing [1-8]. The growing interest in OTES is due to their ability to undergo
polycondensation [9,10] to form a wide range of products [11,12]. The functionalization of
triethoxysilyl moiety with various organic substrates integrates the properties of both organic
and inorganic fragments within a single advanced material [13]. Besides this, the
incorporation of organic functional groups adds hydrophobic character to the surface of
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hybrid material. However, molecular designing of OTES is always a matter of challenge
owing to their moisture sensitivity and complex purification steps. Therefore, it is desirable to
introduce the silyl moiety to the organic fragment in later steps of the reaction [14].
Several synthetic methodologies have been reported in literature for the synthesis of
OTES but the more recent ‘Click Silylation’ overrides the earlier methods owing to its
efficiency, high yields, wide functional group tolerance and anhydrous conditions [15-17].
The use of copper catalyzed azide alkyne cycloaddition (CuAAC) reaction to link the organic
functionality bearing a triple bond with an azide holding triethoxysilyl moiety results into
highly selective synthesis of OTES with challenging substrates. As recently reported by our
group, OTES have also been conjugated to various polyfunctionalized molecular entitites
such as aniline, ether, acrylate, acetate, Schiff base, aldehyde and ketone group via 1,2,3-
triazole linkage [14]. 1,2,3-Triazole is an important scaffold gaining wide popularity these
days. It is known for its stability to oxidative and reductive conditions as well as acid and
base hydrolysis, high dipole moment and hydrogen bond formation [18]. This heterocycle has
been used as an important linker in various organic reactions and has gained significant
progress as a facile building block in biology and material chemistry [19,20].
As a part of our ongoing research on ‘Click Silylation’, we herein introduce
pharmacologically active chalcones as terminal alkyne functionalities. The thought of
working with chalcones stems from their incessant drug like properties and synthetic
accessibility [21]. A wide range of biological activities such as antimalarial [22],
antitubercular [23], anticancer [24], antibacterial [25] and antifungal [26] are known for
chalcone derivatives. They have also been explored extensively for their second-order non-
linear optical (NLO) properties [27]. Considering this, various modifications have been
introduced on the aromatic rings of chalcones resulting into a library of chalconyl blended
triazole encapped triethoxysilanes. All the synthesized compounds have been well
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characterized by various spectroscopic techniques and also screened for their photo-physical
properties.
2. Experimental
2.1 Materials and equipments
Propargyl bromide (80% in toluene) (Aldrich), o/m/p-hydroxyacetophenones (AVERA),
substituted aldehydes (Aldrich), potassium carbonate (Thomas), sodium hydroxide (LOBA
Chemie), sodium sulphate (Finar), Bromotris(triphenylphosphine)copper(I) [CuBr(PPh3)3]
(Aldrich) were used as received. The organic solvents were dried according to standard
procedures [28]. 3-azidopropyltriethoxysilane (AzPTES) and acetylinic chalcones (7a-7e,7h-
7l,7o-9s) were synthesized by known procedure from literature [29,30].
Infrared spectrum was obtained as Neat on a Thermo Scientific Fischer spectrometer. The
13
NMR spectra (1H and C) were recorded on a JEOL (AL 300 MHz) and BRUKER (400
MHz) spectrometer using CDCl3 as internal reference and chemical shifts were reported
relative to tetramethylsilane. J values are given in Hz. The following abbreviations are used:
s, singlet; d, doublet; q, quartet; t, triplet; m, multiplet. Melting points were measured in a
Mel Temp II device using sealed capillaries and were uncorrected. CHN analysis was
obtained on Perkin Elmer Model 2400 CHNS elemental analyzer and Thermo Scientific
Flash 2000 organic elemental analyzer. Electronic spectral measurements were carried out
using JASCO V-530 double beam spectrophotometer and Perkin Elmer LS-55 fluorescence
spectrophotometer. Column chromatography was performed with E. Merck silica gel
(Kieselgel 60, 230-400 mesh). Analytical thin layer chromatography was performed
employing 0.2 mm coated commercial silica gel plates (E. Merck, DC-Aluminum sheets,
Kieselgel 60 F254).
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2.2 General Procedure for the synthesis of acetylinic acetophenones (4/5/6)
2/3/4-hydroxyacetophenone 1/2/3 (1 equiv) was dissolved in 5 ml DMF followed by the
addition of anhydrous K2CO3 (1.5 equiv/ hydroxyacetophenone). The resulting suspension
was stirred for 30 min at room temperature which was then cooled to 0 °C. To this, propargyl
bromide (1.3 equiv/ hydroxyacetophenone) was subsequently added dropwise over a period
of 10 min under stirring and the resulting mixture was allowed to stir at 25 °C for 16 h. The
reaction was monitored by TLC and on consumption of starting materials, quenched by ice
cold water resulting into the formation of precipitate. The precipitate so obtained was filtered,
washed with water and recrystallized from MeOH to afford the crystalline product (4/5/6) in
excellent yield. The spectroscopic data of the resulting compounds correlate well with the
literature reports.
2.3 General Procedure for the synthesis of acetylinic chalcones (7a-7u)
To a solution of the acetylenic acetophenone 4/5/6 (1.0 eq) in MeOH was added 5 ml of
methanolic NaOH (3% w/v). The resulting mixture was stirred at 25°C for 30 min. A
methanolic solution of the commercially available substituted aldehyde (1.0 equiv) was
subsequently added dropwise and the mixture was stirred for a period of 16 h at the same
temperature. The reaction was monitored by TLC and on consumption of starting materials,
quenched by ice cold water resulting into the formation of precipitate (for 7a-g,7l-7u). The
precipitate so obtained was filtered, washed with water and recrystallized from MeOH to
afford the crystalline product. For the reactions in which no precipitation occurred (for 7h-
7k), the product mixture was diluted with water, neutralized with 10% HCl and extracted
with ethyl acetate (20 ml) and the combined organic layers were washed twice with ice cold
water (2×20 ml). The organic layer was dried over anhydrous Na2SO4 and the solvent was
evaporated under reduced pressure to afford yellow brown viscous oil. The crude was then
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subjected to column chromatography with EtOAc/Hexane 3:7, as eluent. The spectroscopic
data of the chalcones 7a-7e,7h-7l and 7o-7s correlate well with the literature reports while the
spectroscopic data of the newly synthesized chalcones 7f,7g,7m,7n,7t,7u is listed below.
(E)-1-(4-(prop-2-ynyloxy)phenyl)-3-p-tolylprop-2-en-1-one (7f)
Yellow solid, Yield: 97 %, M.P.: 104 °C. Anal. Calcd. for C19H16O2: C, 82.58; H, 5.84.
Found: C, 82.47; H, 5.72. IR (neat, cm-1): 1169, 1268 (O-CH2), 1653 (C=O), 2124 (C≡C),
3285 (C≡C-H). 1H (300 MHz, CDCl3, 25 °C): δ 2.33 (s, 3H, CH3), 2.44 (t, J = 2.3 Hz, 1H, -
C≡CH), 4.70 (d, J = 2.3 Hz, 2H, -OCH2-), 6.97 (d, J = 8.8 Hz, 2H, H2, H6), 7.13 (d, J = 7.9
Hz, 2H, H9, H11), 7.40 (d, J = 15.6 Hz, 1H, Hα), 7.45 (d, J = 8.0 Hz, 2H, H8, H12), 7.69 (d,
13
J = 15.6 Hz, 1H, Hβ), 7.96 (d, J = 8.9 Hz, 2H, H3, H5). C (101 MHz, CDCl3, 25 °C): δ
21.5 (CH3), 55.9 (OCH2), 76.2 (C≡CH), 77.8 (C≡CH), 114.7 (C2, C6), 120.8 (Cα), 128.4
(C8, C12), 129.7 (C9, C11), 130.7 (C4), 132.0 (C3, C5), 132.3 (C7), 140.9 (C10), 144.3 (Cβ),
161.1 (C1), 188.8 (C=O).
(E)-3-(4-chlorophenyl)-1-(4-(prop-2-ynyloxy)phenyl)prop-2-en-1-one (7g)
Yellow solid, Yield: 95 %, M.P.: 132 °C. Anal. Calcd. for C18H13ClO2: C, 72.85; H, 4.42.
Found: C, 72.77; H, 4.32. IR (neat, cm-1): 1169, 1265 (O-CH2), 1659 (C=O), 2124 (C≡C),
3294 (C≡C-H). 1H (300 MHz, CDCl3, 25 °C): δ 2.45 (t, J = 2.4 Hz, 1H, -C≡CH), 4.71 (d, J =
2.4 Hz, 2H, -OCH2-), 6.98 (d, J = 8.8 Hz, 2H, H2, H6), 7.32 (d, J = 8.4 Hz, 2H, H9, H11),
7.42 (d, J = 15.6 Hz, 1H, Hα), 7.51 (d, J = 8.5 Hz, 2H, H8, H12), 7.66 (d, J = 15.7 Hz, 1H,
13
Hβ), 7.96 (d, J = 8.8 Hz, 2H, H3, H5). C (101 MHz, CDCl3, 25 °C): δ 55.9 (OCH2), 76.3
(C≡CH), 77.8 (C≡CH), 114.8 (C2, C6), 122.2 (Cα), 129.2 (C8, C12), 129.5 (C9, C11), 130.8
(C4), 131.7 (C3, C5), 133.5 (C7), 136.3 (C10), 142.7 (Cβ), 161.3 (C1), 188.4 (C=O).
(E)-1-(2-(prop-2-ynyloxy)phenyl)-3-p-tolylprop-2-en-1-one (7m)
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Yellow solid, Yield: 92 %, M.P.: 78 °C. Anal. Calcd. for C19H16O2: C, 82.58; H, 5.84. Found:
C, 82.57; H, 5.74. IR (neat, cm-1): 1173, 1263 (O-CH2), 1648 (C=O), 2123 (C≡C), 3295
1
(C≡C-H). H (300 MHz, CDCl3, 25 °C): δ 2.29-2.39 (m, 4H, -C≡CH, CH3), 4.68 (s, 2H, -
OCH2-), 6.98-7.08 (m, 4H, H2, H4, H9, H11), 7.23 (d, J = 15.6 Hz, 1H, Hα), 7.37-7.53 (m,
13
4H, H8, H12, H3, Hβ), 7.65 (d, J = 7.0 Hz, 1H, H5). C (75 MHz, CDCl3, 25 °C): δ 22.0
(CH3), 56.9 (OCH2), 76.6 (C≡CH), 78.8 (C≡CH), 114.0 (C2), 121.5 (C6), 122.4 (Cα), 126.8
(C4), 129.1 (C8, C12), 130.2 (C9, C11), 131.3 (C5), 132.9 (C7), 134.8 (C3), 140.9 (C10),
143.9 (Cβ), 156.6 (C1), 192.6 (C=O).
(E)-3-(4-chlorophenyl)-1-(2-(prop-2-ynyloxy)phenyl)prop-2-en-1-one (7n)
Yellow solid, Yield: 93 %, M.P.: 83 °C. Anal. Calcd. for C18H13ClO2: C, 72.85; H, 4.42.
Found: C, 72.80; H, 4.34. IR (neat, cm-1): 1169, 1256 (O-CH2), 1648 (C=O), 2124 (C≡C),
3297 (C≡C-H). 1H (300 MHz, CDCl3, 25 °C): δ 2.44 (t, J = 2.2 Hz, 1H, -C≡CH), 4.72 (d, J =
2.2 Hz, 2H, -OCH2-), 7.01-7.05 (m, 2H, H2, H4), 7.29 (d, J = 8.3 Hz, 2H, H9, H11), 7.39-
7.44 (m, 2H, H3, Hα), 7.46-7.53 (m, 3H, H8, H12, Hβ), 7.59 (d, J = 6.4 Hz, 1H, H5). 13C (75
MHz, CDCl3, 25 °C): δ 56.3 (OCH2), 76.1 (C≡CH), 78.0 (C≡CH), 113.2 (C2), 121.9 (Cα),
125.7 (C4), 127.5 (C6), 129.1 (C8, C12), 129.5 (C9, C11), 130.9 (C5), 132.8 (C7), 133.8
(C10), 136.1 (C3), 141.3 (Cβ), 156.1 (C1), 191.4 (C=O).
(E)-1-(3-(prop-2-ynyloxy)phenyl)-3-p-tolylprop-2-en-1-one (7t)
Yellow solid, Yield: 96 %, M.P.: 68 °C. Anal. Calcd. for C19H16O2: C, 82.58; H, 5.84. Found:
C, 82.51; H, 5.79. IR (neat, cm-1): 1177, 1274 (O-CH2), 1652 (C=O), 2120 (C≡C), 3276
1
(C≡C-H). H (300 MHz, CDCl3, 25 °C): δ 2.31 (s, 3H, CH3), 2.48 (t, J = 2.4 Hz, 1H, -
C≡CH), 4.69 (d, J = 2.4 Hz, 2H, -OCH2-), 7.11-7.16 (m, 3H, H2, H9, H11), 7.33-7.37 (m,
2H, H2, H6), 7.46 (d, J = 8.1 Hz, 2H, H8, H12), 7.53-7.58 (m, 2H, Hα, H4), 7.72 (d, J = 15.7
Hz, 1H, Hβ). 13C (101 MHz, CDCl3, 25 °C): δ 21.6 (CH3), 56.0 (OCH2), 76.0 (C≡CH), 78.2
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(C≡CH), 114.2 (C6), 119.8 (C2), 121.0 (Cα), 121.9 (C4), 128.5 (C8, C12), 129.7 (C9, C11,
C3), 132.1 (C7), 139.8 (C5), 141.2 (C10), 145.2 (Cβ), 157.8 (C1), 190.2 (C=O).
(E)-3-(4-chlorophenyl)-1-(2-(prop-2-ynyloxy)phenyl)prop-2-en-1-one (7u)
Yellow solid, Yield: 95 %, M.P.: 72 °C. Anal. Calcd. for C18H13ClO2: C, 72.85; H, 4.42.
Found: C, 72.78; H, 4.39. IR (neat, cm-1): 1173, 1268 (O-CH2), 1671 (C=O), 2124 (C≡C),
3447 (C≡C-H). 1H (300 MHz, CDCl3, 25 °C): 2.48 (t, J = 2.4 Hz, 1H, -C≡CH), 4.70 (d, J =
2.4 Hz, 2H, -OCH2-), 7.08 (d, J = 8.4 Hz, 1H, H2), 7.32 (d, J = 8.5 Hz, 2H, H9, H11), 7.36-
7.38 (m, 1H, H3), 7.41 (s, 1H, H6), 7.49 (d, J = 8.4 Hz, 2H, H8, H12), 7.53-7.57 (m, 2H, Hα,
13
H4), 7.68 (d, J = 15.7 Hz, 1H, Hβ). C (101 MHz, CDCl3, 25 °C): δ 56.0 (OCH2), 76.0
(C≡CH), 78.1 (C≡CH), 114.2 (C6), 120.1 (C2), 121.9 (Cα), 122.4 (C4), 128.6 (C8, C12),
129.3 (C9, C11), 129.6 (C3), 133.3 (C7), 136.5 (C5), 139.5 (C10), 143.5 (Cβ), 157.8 (C1),
189.7 (C=O).
2.4 General Procedure for the synthesis of organotriethoxysilanes (8a-8u)
Acetylinic chalcone (1 equiv) was added to 1:1 THF/Et3N solvent mixture taken in a two-
neck round bottomed flask and the mixture was stirred for 15 min at room temperature. Then,
slow addition of AzPTES (1 equiv/alkyne function) was done followed by catalyst
[CuBr(PPh3)3] (0.01 mmol/alkyne function) loading and the mixture was stirred at 60 °C for
5 h. The reaction was then brought to room temperature. The solvents were evaporated under
reduced pressure followed by the addition of hexane. The reaction mixture was then filtered
and concentration of filtrate under reduced pressure afforded the viscous brown silane in
excellent yield.
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-phenylprop-
2-en-1-one (8a) The quantities used were as 7a (1.0 g, 3.8 mmol), AzPTES (0.94 g, 3.8
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mmol). Brown oil, Yield: 1.81 g, 93 %. Anal. Calcd. for C27H35N3O5Si: C, 63.63; H, 6.92; N,
8.24. Found: C, 63.58; H, 6.82; N, 8.13. IR (neat, cm-1): 768, 1073 (Si-O), 1649 (C=O), 2972
1
(C=C-H). H NMR (300 MHz, CDCl3, 25°C): δ 0.50 (m, 2H, -SiCH2-), 1.14 (t, J = 6.9 Hz,
9H, -OCH2CH3), 1.96 (m, 2H, -CCH2C-), 3.72 (q, J = 6.9 Hz, 6H, -OCH2CH3), 4.30 (t, J =
7.0 Hz, 2H, -N3CH2-), 5.23 (s, 2H, -OCH2-), 7.00 Hz (d, J = 8.6 Hz, 2H, H2, H6), 7.19-7.54
(m, 5H, Ar-H), 7.44 (d, J = 15.7 Hz, 1H, Hα), 7.54 (s, 1H, Tz-H), 7.70 (d, J = 15.6 Hz, 1H,
13
Hβ), 7.95 (d, J = 8.6 Hz, 2H, H3, H5). C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ 7.0
(SiCH2), 17.9 (OCH2CH3), 23.7 (CCH2C), 51.9 (N3CH2), 58.0 (OCH2CH3), 61.8 (OCH2),
114.3 (C2, C6), 121.4, 141.4 (Tz-C), 122.2 (Cα), 128.0 (C8, C12), 128.5 (C10), 129.1 (C9,
C11), 129.9 (C4), 130.4 (C3, C5), 131.3 (C7), 143.6 (Cβ), 161.6 (C1), 190.5 (C=O).
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-methoxy
phenyl)prop-2-en-1-one (8b) The quantities used were as 7b (1.0 g, 3.4 mmol), AzPTES
(0.85 g, 3.4 mmol). Brown oil, Yield: 1.68 g, 91 %. Anal. Calcd. for C28H37N3O6Si: C, 62.31;
H, 6.91; N, 7.79. Found: C, 62.28; H, 6.80; N, 7.63. IR (neat, cm-1): 781, 1078 (Si-O), 1661
(C=O), 2974 (C=C-H). 1H NMR (300 MHz, CDCl3, 25 °C): δ 0.42 (m, 2H, -SiCH2-), 1.16 (t,
J = 7.0 Hz, 9H, -OCH2CH3), 1.82 (m, 2H, -CCH2C-), 3.73 (q, J = 7.0 Hz, 6H, -OCH2CH3),
3.81 (s, 3H, -OCH3), 4.08 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.26 (s, 2H, -OCH2-), 6.84 (d, J = 8.7
Hz, 2H, H9, H11), 7.02-7.09 (m, 3H, Tz-H, H2, H6), 7.22 (d, J = 15.8 Hz, 1H, Hα), 7.41 (d,
J = 8.7 Hz, 2H, H8, H12), 7.47 (s, 1H, Tz-H), 7.50 (d, J = 15.8 Hz, 1H, Hβ), 7.59 (d, J = 9.1
Hz, 2H, H3, H5). 13C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ 7.5 (SiCH2), 18.4 (OCH2CH3),
24.2 (CCH2C), 52.4 (N3CH2), 55.3 (OCH3), 58.5 (OCH2CH3), 63.3 (OCH2), 113.2 (C9, C11),
114.6 (C2, C6), 121.6, 141.2 (Tz-C), 122.6 (Cα), 125.6 (C8, C12), 128.1 (C7), 130.3 (C4),
130.8 (C3, C5), 142.7 (Cβ), 157.0 (C10), 162.7 (C1), 189.4 (C=O).
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2-methoxy
phenyl)prop-2-en-1-one (8c) The quantities used were as 7c (1.0 g, 3.4 mmol), AzPTES
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(0.85 g, 3.4 mmol). Brown oil, Yield: 1.70 g, 92 %. Anal. Calcd. for C28H37N3O6Si: C, 62.31;
H, 6.91; N, 7.79. Found: C, 62.23; H, 6.85; N, 7.68. IR (neat, cm-1): 781, 1076 (Si-O), 1650
(C=O), 2964 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.50 (m, 2H, -SiCH2-), 1.14 (t,
J = 7.0 Hz, 9H, -OCH2CH3), 1.96 (m, 2H, -CCH2C-), 3.71 (q, J = 7.0 Hz, 6H, -OCH2CH3),
3.86 (s, 3H, -OCH3), 4.29 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.22 (s, 2H, -OCH2-), 6.83-7.26 (m,
6H, Ar-H), 7.50 (d, J = 15.8 Hz, 1H, Hα), 7.54 (s, 1H, Tz-H), 7.94 (d, J = 8.7 Hz, 2H, H3,
H5), 7.99 (d, J = 15.8 Hz, 1H, Hβ). 13C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ 7.7 (SiCH2),
18.6 (OCH2CH3), 24.5 (CCH2C), 52.7 (N3CH2), 55.7 (OCH3), 58.7 (OCH2CH3), 62.5
(OCH2), 111.5 (C11), 114.9 (C2, C6), 115.5 (C7), 121.1, 140.0 (Tz-C), 123.0 (Cα), 127.5
(C9), 129.6 (C8), 130.2 (C10), 131.3 (C4), 131.8 (C3, C5), 143.8 (Cβ), 159.2 (C12), 162.2
(C1), 190.1 (C=O).
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,4-
dimethoxy phenyl)prop-2-en-1-one (8d) The quantities used were as 7d (1.0 g, 3.1 mmol),
AzPTES (0.77 g, 3.1 mmol). Brown oil, Yield: 1.57 g, 89 %. Anal. Calcd. for C29H39N3O7Si:
C, 61.14; H, 6.90; N, 7.38. Found: C, 61.09; H, 6.81; N, 7.27. IR (neat, cm-1): 755, 1078 (Si-
O), 1654 (C=O), 2974 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.49 (m, 2H, -SiCH2-
), 1.13 (t, J = 6.9 Hz, 9H, -OCH2CH3), 1.96 (m, 2H, -CCH2C-), 3.69-3.82 (m, 12H, 2×-OCH3,
-OCH2CH3), 4.28 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.18 (s, 2H, -OCH2-), 6.35 (s, 1H, H11), 6.40
(d, J = 7.0 Hz, 1H, H9), 6.94 (d, J = 8.5 Hz, 2H, H2, H6), 7.38-7.46 (m, 2H, Hα, H8), 7.55 (s,
1H, Tz-H), 7.87-7.92 (m, 3H, H3, H5, Hβ). 13C NMR (75 MHz, CDCl3, 25 °C): δ 7.1
(SiCH2), 18.1 (OCH2CH3), 24.0 (CCH2C), 52.1 (N3CH2), 55.2 (2×OCH3,), 58.2 (OCH2CH3),
61.9 (OCH2), 98.2 (C11), 105.2 (C9), 114.3 (C7), 117.1 (C2, C6), 119.8, 139.4 (Tz-C), 122.6
(Cα), 128.4 (C8), 130.5 (C4), 132.0 (C3, C5), 143.2 (Cβ), 160.1 (C12), 161.5 (C10), 162.7
(C1), 188.5 (C=O).
10

ACCEPTED MANUSCRIPT
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,3,4-
trimethoxyphenyl)prop-2-en-1-one (8e) The quantities used were as 7e (1.0 g, 2.8 mmol),
AzPTES (0.70 g, 2.8 mmol). Brown oil, Yield: 1.53 g, 90 %. Anal. Calcd. for C30H41N3O8Si:
C, 60.08; H, 6.89; N, 7.01. Found: C, 59.98; H, 6.81; N, 6.97. IR (neat, cm-1): 757, 1075 (Si-
O), 1655 (C=O), 2973 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.48 (m, 2H, -SiCH2-
), 1.13 (t, J = 7.0 Hz, 9H, -OCH2CH3), 1.95 (m, 2H, -CCH2C-), 3.71 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 3.79 (s, 3H, -OCH3), 3.83 (s, 3H, -OCH3), 3.87 (s, 3H, -OCH3), 4.28 (t, J = 7.1
Hz, 2H, -N3CH2-), 5.20 (s, 2H, -OCH2-), 6.59 (d, J = 8.7 Hz, 1H, H9), 6.96 (d, J = 8.7 Hz,
1H, H8), 7.25 (d, J = 8.7 Hz, 2H, H2, H6), 7.44 (d, J = 15.7 Hz, 1H, Hα), 7.54 (s, 1H, Tz-H),
7.82 (d, J = 15.7 Hz, 1H, Hβ), 7.92 (d, J = 8.7 Hz, 2H, H3, H5). 13C NMR (75 MHz,
CDCl3/CCl4, 25 °C): δ 7.4 (SiCH2), 18.3 (OCH2CH3), 24.2 (CCH2C), 52.3 (N3CH2), 55.9
(OCH3), 58.4 (OCH2CH3), 60.7 (OCH3), 61.2 (OCH3), 62.2 (OCH2), 107.7 (C7, C9), 114.6
(C2, C6), 121.2 (C8), 122.5, 139.3 (Tz-C), 123.8 (Cα), 130.7 (C4), 132.1 (C3, C5), 142.8
(C11), 143.4 (Cβ), 154.0 (C12), 155.7 (C10), 161.9 (C1), 188.3 (C=O).
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-p-tolylprop-
2-en-1-one (8f) The quantities used were as 7f (1.0 g, 3.6 mmol), AzPTES (0.89 g, 3.6
mmol). Brown oil, Yield: 1.72 g, 91 %. Anal. Calcd. for C28H37N3O5Si: C, 64.22; H, 7.12; N,
8.02. Found: C, 64.13; H, 7.03; N, 7.93. IR (neat, cm-1): 782, 1099 (Si-O), 1656 (C=O), 2973
1
(C=C-H). H NMR (300 MHz, CDCl3, 25°C): δ 0.48 (m, 2H, -SiCH2-), 1.13 (t, J = 6.9 Hz,
9H, -OCH2CH3), 1.95 (m, 2H, -CCH2C-), 2.31 (s, 3H, -CH3), 3.71 (q, J = 6.9 Hz, 6H, -
OCH2CH3), 4.28 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.20 (s, 2H, -OCH2-), 6.96 (d, J = 8.6 Hz, 2H,
H2, H6), 7.10 (d, J = 7.9 Hz, 2H, H9, H11), 7.35-7.44 (m, 3H, H8, H12, Hα), 7.54 (s, 1H, Tz-
13
H), 7.65 (d, J = 15.6 Hz, 1H, Hβ), 7.92 (d, J = 8.6 Hz, 2H, H3, H5). C NMR (75 MHz,
CDCl3/CCl4, 25 °C): δ 7.6 (SiCH2), 18.5 (OCH2CH3), 21.7 (CH3), 24.4 (CCH2C), 52.6
(N3CH2), 58.6 (OCH2CH3), 62.5 (OCH2), 114.9 (C2, C6), 121.0, 140.8 (Tz-C), 122.9 (Cα),
11

ACCEPTED MANUSCRIPT
128.7 (C8, C12), 130.0 (C9, C11), 131.1 (C4, C7), 132.1 (C3, C5), 132.8 (C10), 144.3 (Cβ),
162.2 (C1), 188.2 (C=O).
(E)-1-(4-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-chloro
phenyl)prop-2-en-1-one (8g) The quantities used were as 7g (1.0 g, 3.4 mmol), AzPTES
(0.83 g, 3.4 mmol). Brown oil, Yield: 1.63 g, 89 %. Anal. Calcd. for C27H34ClN3O5Si: C,
59.60; H, 6.30; N, 7.72. Found: C, 59.48; H, 6.23; N, 7.68. IR (neat, cm-1): 762, 1080 (Si-O),
1
1660 (C=O), 2927 (C=C-H). H NMR (300 MHz, CDCl3, 25°C): δ 0.51 (m, 2H, -SiCH2-),
1.15 (t, J = 6.9 Hz, 9H, -OCH2CH3), 1.97 (m, 2H, -CCH2C-), 3.73 (q, J = 6.9 Hz, 6H, -
OCH2CH3), 4.30 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.23 (s, 2H, -OCH2-), 7.00 (d, J = 8.6 Hz, 2H,
H2, H6), 7.31 (d, J = 9.7 Hz, 2H, H9, H11), 7.43 (d, J = 9.7 Hz, 2H, H8, H12), 7.46 (d, J =
15.3 Hz, 1H, Hα), 7.54 (s, 1H, Tz-H), 7.65 (d, J = 15.3 Hz, 1H, Hβ), 7.94 (d, J = 8.6 Hz, 2H,
13
H3, H5). C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ 7.7 (SiCH2), 18.6 (OCH2CH3), 24.4
(CCH2C), 52.6 (N3CH2), 58.7 (OCH2CH3), 62.5 (OCH2), 115.0 (C2, C6), 122.5, 136.6 (Tz-
C), 122.5 (Cα), 129.6 (C8, C12), 129.8 (C9, C11), 131.1 (C4), 132.5 (C3, C5), 134.0 (C7),
134.5 (C10), 142.7 (Cβ), 162.5 (C1), 187.9 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-phenylprop-
2-en-1-one (8h) The quantities used were as 7h (1.0 g, 3.8 mmol), AzPTES (0.94 g, 3.8
mmol). Brown oil, Yield: 1.73 g, 89 %. Anal. Calcd. for C27H35N3O5Si: C, 63.63; H, 6.92; N,
8.24. Found: C, 63.54; H, 6.80; N, 8.09. IR (neat, cm-1): 753, 1094 (Si-O), 1659 (C=O), 2933
1
(C=C-H). H NMR (300 MHz, CDCl3, 25°C): δ 0.35 (m, 2H, -SiCH2-), 1.12 (t, J = 7.0 Hz,
9H, -OCH2CH3), 1.75 (m, 2H, -CCH2C-), 3.69 (q, J = 7.0 Hz, 6H, -OCH2CH3), 4.00 (t, J =
7.0 Hz, 2H, -N3CH2-), 5.22 (s, 2H, -OCH2-), 6.95-7.06 (m, 3H, H2, H4, H10), 7.27-7.42 (m,
6H, H9, H11, H8, H12, Tz-H, H3), 7.49 (d, J = 15.9 Hz, 1H, Hα), 7.57 (d, J = 15.1 Hz, 1H,
13
Hβ), 7.97 (d, J = 7.4 Hz, 1H, H5). C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ 7.4 (SiCH2),
18.4 (OCH2CH3), 23.7 (CCH2C), 52.2 (N3CH2), 58.4 (OCH2CH3), 62.8 (OCH2), 113.0 (C2),
12

ACCEPTED MANUSCRIPT
121.2, 142\.1 (Tz-C), 121.3 (C6), 122.5 (C4), 121.5 (Cα), 127.6 (C8, C12), 128.2 (C10),
128.5 (C9, C11), 129.0 (C5), 130.2 (C7), 131.0 (C3), 143.5 (Cβ), 157.1 (C1), 191.5 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-
methoxyphenyl)prop-2-en-1-one (8i) The quantities used were as 7i (1.0 g, 3.4 mmol),
AzPTES (0.85 g, 3.4 mmol). Brown oil, Yield: 1.68 g, 91 %. Anal. Calcd. for C28H37N3O6Si:
C, 62.31; H, 6.91; N, 7.79. Found: C, 62.23; H, 6.81; N, 7.64. IR (neat, cm-1): 783, 1073 (Si-
O), 1654 (C=O), 2973 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.38 (m, 2H, -SiCH2-
), 1.12 (t, J = 7.0 Hz, 9H, -OCH2CH3), 1.78 (m, 2H, -CCH2C-), 3.69 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 3.76 (s, 3H, -OCH3), 4.04 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.22 (s, 2H, -OCH2-),
6.80 (d, J = 8.7 Hz, 2H, H9, H11), 6.90 (d, J = 8.7 Hz, 1H, H2), 6.95-7.05 (m, 3H, C4, C8,
C12), 7.18 (d, J = 15.8 Hz, 1H, Hα), 7.35 (s, 1H, Tz-H), 7.38-7.40 (m, 1H, H3), 7.46 (d, J =
15.6 Hz, 1H, Hβ), 7.73 (d, J = 8.7 Hz, 1H, H5). 13C NMR (75 MHz, CDCl3/CCl4, 25 °C): δ
7.4 (SiCH2), 18.4 (OCH2CH3), 24.1 (CCH2C), 52.3 (N3CH2), 55.3 (OCH3), 58.5 (OCH2CH3),
63.2 (OCH2), 113.2 (C9, C11), 114.5 (C2), 125.5 (C6), 121.6, 142.5 (Tz-C), 122.7 (Cα),
130.8 (C7), 128.0 (C4), 130.2 (C8, C12), 132.0 (C5), 132.9 (C3), 143.3 (Cβ), 157.0 (C10),
161.7 (C1), 192.1 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2-methoxy
phenyl)prop-2-en-1-one (8j) The quantities used were as 7j (1.0 g, 3.4 mmol), AzPTES (0.85
g, 3.4 mmol). Brown oil, Yield: 1.64 g, 89 %. Anal. Calcd. for C28H37N3O6Si: C, 62.31; H,
6.91; N, 7.79. Found: C, 62.18; H, 6.78; N, 7.61. IR (neat, cm-1): 779, 1078 (Si-O), 1660
(C=O), 2975 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.37 (m, 2H, -SiCH2-), 1.12 (t,
J = 6.9 Hz, 9H, -OCH2CH3), 1.77 (m, 2H, -CCH2C-), 3.69 (q, J = 7.0 Hz, 6H, -OCH2CH3),
3.77 (s, 3H, -OCH3), 4.01 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.23 (s, 2H, -OCH2-), 6.81-7.05 (m,
5H, H2, H4, H9-H11), 7.24 (d, J = 7.2 Hz, 1H, H8), 7.36 (d, J = 15.9 Hz, 1H, Hα), 7.41 (s,
13
1H, Tz-H), 7.52-7.76 (m, 2H, H3, H5), 7.83 (d, J = 16.0 Hz, 1H, Hβ). C NMR (75 MHz,
13

ACCEPTED MANUSCRIPT
CDCl3/CCl4, 25 °C): δ 7.4 (SiCH2), 18.3 (OCH2CH3), 24.1 (CCH2C), 52.3 (N3CH2), 55.4
(OCH3), 58.4 (OCH2CH3), 63.4 (OCH2), 111.2 (C11), 113.1 (C2), 120.8 (C9), 120.9 (C6),
121.5, 138.0 (Tz-C), 122.6 (Cα, C7), 124.3 (C4), 128.1 (C8), 128.9 (C10), 130.8 (C5), 135.7
(C3), 145.6 (Cβ), 157.0 (C12), 158.8 (C1), 192.6 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,4-di
methoxyphenyl)prop-2-en-1-one (8k) The quantities used were as 7k (1.0 g, 3.1 mmol),
AzPTES (0.77 g, 3.1 mmol). Brown oil, Yield: 1.57 g, 89 %. Anal. Calcd. for C29H39N3O7Si:
C, 61.14; H, 6.90; N, 7.38. Found: C, 60.98; H, 6.81; N, 7.26. IR (neat, cm-1): 752, 1072 (Si-
O), 1651 (C=O), 2972 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.38 (m, 2H, -SiCH2-
), 1.12 (t, J = 6.8 Hz, 9H, -OCH2CH3), 1.77 (m, 2H, -CCH2C-), 3.68 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 3.74 (s, 3H, -OCH3), 3.76 (s, 3H, -OCH3), 4.04 (t, J = 6.9 Hz, 2H, -N3CH2-),
5.21 (s, 2H, -OCH2-), 6.33 (s, 1H, H11), 6.39 (d, J = 8.4 Hz, 1H, H9), 6.94-7.03 (m, 3H, H2,
H4, H8), 7.23 (d, J = 15.8 Hz, 1H, Hα), 7.32-7.38 (m, 1H, H3), 7.41 (s, 1H, Tz-H), 7.53 (d, J
= 7.5 Hz, 1H, H5), 7.74 (d, J = 15.8 Hz, 1H, Hβ). 13C NMR (101 MHz, CDCl3, 25 °C): δ 7.2
(SiCH2), 18.0 (OCH2CH3), 23.9 (CCH2C), 52.2 (N3CH2), 55.8 (OCH3), 57.6 (OCH3), 58.3
(OCH2CH3), 62.8 (OCH2), 100.3 (C11), 106.4 (C9), 107.5 (C7), 112.9 (C2), 121.1, 142.1
(Tz-C), 121.7 (Cα), 122.6 (C6), 123.0 (C4), 126.1 (C8), 130.2 (C5), 132.5 (C3), 143.5 (Cβ),
156.4 (C12), 157.2 (C10), 161.0 (C1), 192.7 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,3,4-tri
methoxyphenyl)prop-2-en-1-one (8l) The quantities used were as 7l (1.0 g, 2.8 mmol),
AzPTES (0.70 g, 2.8 mmol). Brown oil, Yield: 1.53 g, 90 %. Anal. Calcd. for C30H41N3O8Si:
C, 60.08; H, 6.89; N, 7.01. Found: C, 60.02; H, 6.83; N, 6.94. IR (neat, cm-1): 783, 1093 (Si-
O), 1670 (C=O), 2972 (C=C-H). 1H NMR (300 MHz, CDCl3, 25°C): δ 0.41 (m, 2H, -SiCH2-
), 1.08 (t, J = 7.0 Hz, 9H, -OCH2CH3), 1.79 (m, 2H, -CCH2C-), 3.74 (m, 15H, 3×-OCH3, -
OCH2CH3), 4.09 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.19 (s, 2H, -OCH2-), 6.58 (d, J = 9.0 Hz, 1H,
14

ACCEPTED MANUSCRIPT
H9), 6.95-7.15 (m, 3H, H8, H2, H4), 7.27-7.34 (m, 1H, H3), 7.41 (s, 1H, Tz-H), 7.47-7.58
13
(m, 2H, Hα, H5), 7.69 (d, J = 15.7 Hz, 1H, Hβ). C NMR (101 MHz, CDCl3, 25 °C): δ 7.3
(SiCH2), 18.2 (OCH2CH3), 24.0 (CCH2C), 52.3 (N3CH2), 56.0 (OCH3), 58.4 (OCH2CH3),
60.7 (OCH3), 61.4 (OCH3), 62.9 (OCH2), 106.5 (C9), 107.6 (C7), 113.0 (C2), 121.3 (C8),
121.9 (C6), 122.8, 142.2 (Tz-C), 123.1 (Cα), 126.2 (C4), 130.3 (C5), 132.6 (C3), 138.0
(C11), 143.6 (Cβ), 153.5 (C12), 155.5 (C10), 156.5 (C1), 192.8 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-p-tolyl-prop
-2-en-1-one (8m) The quantities used were as 7m (1.0 g, 3.6 mmol), AzPTES (0.89 g, 3.6
mmol). Brown oil, Yield: 1.67 g, 88 %. Anal. Calcd. for C28H37N3O5Si: C, 64.22; H, 7.12; N,
8.02. Found: C, 64.18; H, 7.06; N, 7.91. IR (neat, cm-1): 781, 1078 (Si-O), 1660 (C=O), 2974
1
(C=C-H). H NMR (300 MHz, CDCl3, 25°C): δ 0.36 (m, 2H, -SiCH2-), 1.12 (t, J = 6.9 Hz,
9H, -OCH2CH3), 1.77 (m, 2H, -CCH2C-), 2.31 (s, 3H, CH3), 3.69 (q, J = 6.9 Hz, 6H, -
OCH2CH3), 4.01 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.21 (s, 2H, -OCH2-), 6.95-7.10 (m, 4H, H2,
H4, H9, H11), 7.31 (d, J = 8.0 Hz, 2H, H8, H12), 7.35-7.38 (m, 2H, Tz-H, H3), 7.47 (d, J =
15.9 Hz, 1H, Hα), 7.56 (d, J = 15.6 Hz, 1H, Hβ), 7.67 (d, J = 7.6 Hz, 1H, H5). 13C NMR (75
MHz, CDCl3/CCl4, 25 °C): δ 7.4 (SiCH2), 18.3 (OCH2CH3), 21.5 (CH3), 24.0 (CCH2C), 52.2
(N3CH2), 58.4 (OCH2CH3), 63.1 (OCH2), 113.0 (C2), 121.5, 140.5 (Tz-C), 121.5 (Cα), 122.6
(C4, C6), 126.7 (C8, C12), 128.5 (C9, C11), 129.7 (C5), 130.8 (C7), 132.5 (C3), 133.0 (C10),
142.5 (Cβ), 157.0 (C1), 191.9 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-chloro
phenyl)prop-2-en-1-one (8n) The quantities used were as 7n (1.0 g, 3.4 mmol), AzPTES
(0.83 g, 3.4 mmol). Brown oil, Yield: 1.61 g, 88 %. Anal. Calcd. for C27H34ClN3O5Si: C,
59.60; H, 6.30; N, 7.72. Found: C, 59.52; H, 6.28; N, 7.63. IR (neat, cm-1): 785, 1073 (Si-O),
1
1654 (C=O), 2972 (C=C-H). H NMR (400 MHz, CDCl3, 25°C): δ 0.43 (m, 2H, -SiCH2-),
1.12 (t, J = 6.9 Hz, 9H, -OCH2CH3), 1.82 (m, 2H, -CCH2C-), 3.70 (q, J = 6.9 Hz, 6H, -
15

ACCEPTED MANUSCRIPT
OCH2CH3), 4.10 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.22 (s, 2H, -OCH2-), 6.99 (t, J = 7.4 Hz, 1H,
H4), 7.06 (d, J = 8.3 Hz, 1H, H2), 7.27 (d, J = 8.3 Hz, 2H, H9, H11), 7.32 (s, 1H, Tz-H), 7.35
(d, J = 8.0 Hz, 2H, H8, H12), 7.39-7.42 (m, 2H, Hα, H3), 7.46 (d, J = 15.9 Hz, 1H, Hβ), 7.60
(d, J = 7.3 Hz, 1H, H5). 13C NMR (75 MHz, CDCl3, 25 °C): δ 7.2 (SiCH2), 18.2 (OCH2CH3),
24.0 (CCH2C), 52.3 (N3CH2), 58.4 (OCH2CH3), 62.8 (OCH2), 112.8 (C2), 121.4, 140.8 (Tz-
C), 121.4 (Cα), 122.6 (C4, C6), 127.6 (C8, C12), 129.0 (C9, C11), 129.4 (C5), 130.6 (C7),
133.3 (C10), 135.9 (C3), 143.1 (Cβ), 156.9 (C1), 191.8 (C=O).
(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-phenylprop-
2-en-1-one (8o) The quantities used were as 7o (1.0 g, 3.8 mmol), AzPTES (0.94 g, 3.8
mmol). Brown oil, Yield: 1.77 g, 91 %. Anal. Calcd. for C27H35N3O5Si: C, 63.63; H, 6.92; N,
8.24. Found: C, 63.51; H, 6.78; N, 8.11. IR (neat, cm-1): 760, 1075 (Si-O), 1663 (C=O), 2975
1
(C=C-H). H NMR (400 MHz, CDCl3, 25°C): δ 0.61 (m, 2H, -SiCH2-), 1.22 (t, J = 7.0 Hz,
9H, -OCH2CH3), 2.04 (m, 2H, -CCH2C-), 3.81 (q, J = 7.0 Hz, 6H, -OCH2CH3), 4.37 (t, J =
7.0 Hz, 2H, -N3CH2-), 5.28 (s, 2H, -OCH2-), 7.22 (d, J = 8.0 Hz, 1H, H2), 7.35-7.43 (m, 4H,
H9-H11, Tz-H), 7.52 (d, J = 15.7 Hz, 1H, Hα), 7.62-7.68 (m, 5H, H8, H12, H3, H4, H6),
13
7.81 (d, J = 15.7 Hz, 1H, Hβ). C NMR (101 MHz, CDCl3, 25 °C): δ 7.2 (SiCH2), 18.1
(OCH2CH3), 24.0 (CCH2C), 52.3 (N3CH2), 58.3 (OCH2CH3), 62.0 (OCH2), 114.0 (C6),
119.2 (C2), 120.5, 140.4 (Tz-C), 121.3 (Cα), 122.5 (C4), 125.9 (C8, C12), 128.2 (C10), 128.3
(C9, C11), 129.1 (C3), 131.6 (C7), 139.7 (C5), 143.3 (Cβ), 158.6 (C1), 190.5 (C=O).
(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-methoxy
phenyl)prop-2-en-1-one (8p) The quantities used were as 7p (1.0 g, 3.4 mmol), AzPTES
(0.85 g, 3.4 mmol). Brown oil, Yield: 1.70 g, 92 %. Anal. Calcd. for C28H37N3O6Si: C, 62.31;
H, 6.91; N, 7.79. Found: C, 62.23; H, 6.85; N, 7.73. IR (neat, cm-1): 722, 1075 (Si-O), 1659
(C=O), 2975 (C=C-H). 1H NMR (400 MHz, CDCl3, 25°C): δ 0.61 (m, 2H, -SiCH2-), 1.21 (t,
J = 7.0 Hz, 9H, -OCH2CH3), 2.04 (m, 2H, -CCH2C-), 3.81 (q, J = 7.0 Hz, 6H, -OCH2CH3),
16

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3.84 (s, 3H, OCH3), 4.37 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.28 (s, 2H, -OCH2-), 6.93 (d, J = 8.7
Hz, 2H, H9, H11), 7.20 (d, J = 8.1 Hz, 1H, H2), 7.38-7.43 (m, 3H, H6, H8, H12), 7.60-7.66
(m, 3H, H3, H4, Hα), 7.68 (s, 1H, Tz-H), 7.79 (d, J = 15.6 Hz, 1H, Hβ). 13C NMR (101 MHz,
CDCl3, 25 °C): δ 7.4 (SiCH2), 18.3 (OCH2CH3), 24.2 (CCH2C), 52.5 (N3CH2), 55.4 (OCH3),
58.5 (OCH2CH3), 62.1 (OCH2), 114.2 (C6), 114.4 (C9, C11), 119.4 (C2), 119.6, 143.5 (Tz-
C), 121.4 (Cα), 122.9 (C4), 127.5 (C8, C12), 129.7 (C7), 130.3 (C3), 139.9 (C5), 144.9 (Cβ),
158.5 (C10), 161.7 (C1), 190.1 (C=O).
(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2-methoxy
phenyl)prop-2-en-1-one (8q) The quantities used were as 7q (1.0 g, 3.4 mmol), AzPTES
(0.85 g, 3.4 mmol). Brown oil, Yield: 1.68 g, 91 %. Anal. Calcd. for C28H37N3O6Si: C, 62.31;
H, 6.91; N, 7.79. Found: C, 62.26; H, 6.83; N, 7.69. IR (neat, cm-1): 722, 1075 (Si-O), 1660
(C=O), 2975 (C=C-H). 1H NMR (400 MHz, CDCl3, 25°C): δ 0.61 (m, 2H, -SiCH2-), 1.21 (t,
J = 7.0 Hz, 9H, -OCH2CH3), 2.04 (m, 2H, -CCH2C-), 3.81 (q, J = 7.0 Hz, 6H, -OCH2CH3),
3.91 (s, 3H, OCH3), 4.37 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.28 (s, 2H, -OCH2-), 6.94 (d, J = 8.0
Hz, 1H, H11), 6.99 (t, J = 8.0 Hz, 1H, H9), 7.21 (d, J = 8.2 Hz, 1H, H2), 7.36-7.39 (m, 1H,
H10), 7.42 (d, J = 8.0 Hz, 1H, H8), 7.58 (s, 1H, Tz-H), 7.62-7.67 (m, 4H, H3, H4, H6, Hα),
13
8.13 (d, J = 15.9 Hz, 1H, Hβ). C NMR (101 MHz, CDCl3, 25 °C): δ 7.6 (SiCH2), 18.4
(OCH2CH3), 24.3 (CCH2C), 52.6 (N3CH2), 55.7 (OCH3), 58.6 (OCH2CH3), 62.3 (OCH2),
111.3 (C6), 114.3 (C11), 119.5 (C7), 120.9, 140.7 (Tz-C), 121.6 (C2), 122.8 (Cα), 122.9
(C9), 124.0 (C4), 129.4 (C8), 129.8 (C10), 131.9 (C3), 140.1 (C5), 143.7 (Cβ), 158.6 (C12),
158.9 (C1), 190.8 (C=O).
(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,4-di
methoxyphenyl)prop-2-en-1-one (8r) The quantities used were as 7r (1.0 g, 3.1 mmol),
AzPTES (0.77 g, 3.1 mmol). Brown oil, Yield: 1.64 g, 93 %. Anal. Calcd. for C29H39N3O7Si:
C, 61.14; H, 6.90; N, 7.38. Found: C, 61.06; H, 6.83; N, 7.29. IR (neat, cm-1): 755, 1077 (Si-
17

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O), 1657 (C=O), 2974 (C=C-H). 1H NMR (400 MHz, CDCl3, 25°C): δ 0.63 (m, 2H, -SiCH2-
), 1.24 (t, J = 7.0 Hz, 9H, -OCH2CH3), 2.06 (m, 2H, -CCH2C-), 3.72 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 3.88 (s, 3H, -OCH3), 3.91 (s, 3H, -OCH3), 4.36 (t, J = 7.2 Hz, 2H, -N3CH2-),
5.22 (s, 2H, -OCH2-), 6.23 (s, 1H, H11), 6.55 (d, J = 9.0 Hz, 1H, H9), 7.45-7.48 (m, 2H, H2,
H8), 7.54-7.57 (m, 2H, Tz-H, H6), 7.64-7.69 (m, 2H, Hα, H3), 7.81 (d, J = 8.6 Hz, 1H, H4),
13
8.04 (d, J = 15.5 Hz, 1H, Hβ). C NMR (101 MHz, CDCl3, 25 °C): δ 8.9 (SiCH2), 18.5
(OCH2CH3), 24.4 (CCH2C), 55.5 (N3CH2), 55.6 (OCH3), 55.7 (OCH3), 58.4 (OCH2CH3),
62.0 (OCH2), 98.0 (C11), 104.9 (C9), 105.8 (C7), 114.1 (C6), 120.1, 142.5 (Tz-C), 120.7
(C2), 121.4 (Cα), 123.4 (C4), 128.5 (C8), 130.8 (C3), 132.2 (C5), 144.6 (Cβ), 158.5 (C12),
160.5 (C10), 163.6 (C1), 188.4 (C=O).
(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(2,3,4-tri
methoxyphenyl)prop-2-en-1-one (8s) The quantities used were as 7s (1.0 g, 2.8 mmol),
AzPTES (0.70 g, 2.8 mmol). Brown oil, Yield: 1.56 g, 92 %. Anal. Calcd. for C30H41N3O8Si:
C, 60.08; H, 6.89; N, 7.01. Found: C, 59.91; H, 6.78; N, 6.93. IR (neat, cm-1): 723, 1096 (Si-
O), 1658 (C=O), 2974 (C=C-H). 1H NMR (400 MHz, CDCl3, 25°C): δ 0.62 (m, 2H, -SiCH2-
), 1.22 (t, J = 7.0 Hz, 9H, -OCH2CH3), 2.05 (m, 2H, -CCH2C-), 3.81 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 3.89 (s, 3H, -OCH3), 3.91 (s, 3H, -OCH3), 3.95 (s, 3H, -OCH3), 4.38 (t, J = 7.2
Hz, 2H, -N3CH2-), 5.28 (s, 2H, -OCH2-), 6.7 (d, J = 8.0 Hz, 1H, H9), 7.21 (d, J = 8.0 Hz, 1H,
H8), 7.39-7.43 (m, 2H, H2, H6), 7.54 (d, J = 15.8 Hz, 1H, Hα), 7.62-7.66 (m, 2H, H3, H4),
7.69 (s, 1H, Tz-H), 8.02 (d, J = 15.8 Hz, 1H, Hβ). 13C NMR (101 MHz, CDCl3, 25 °C): δ 7.5
(SiCH2), 18.3 (OCH2CH3), 24.2 (CCH2C), 52.6 (N3CH2), 56.1 (OCH3), 58.6 (OCH2CH3),
60.9 (OCH3), 61.5 (OCH3), 62.2 (OCH2), 107.7 (C9), 114.2 (C12), 119.4 (C6), 121.2 (C2),
121.4 (C8), 122.0, 142.5 (Tz-C), 122.9 (Cα), 123.4 (C4), 129.7 (C3), 140.1 (C5), 140.3
(C11), 143.6 (Cβ), 153.9 (C12), 155.9 (C10), 158.5 (C1), 190.4 (C=O).
18

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(E)-1-(3-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-p-tolyl-prop
-2-en-1-one (8t) The quantities used were as 7t (1.0 g, 3.6 mmol), AzPTES (0.89 g, 3.6
mmol). Brown oil, Yield: 1.70 g, 90 %. Anal. Calcd. for C28H37N3O5Si: C, 64.22; H, 7.12; N,
8.02. Found: C, 64.10; H, 6.98; N, 7.96. IR (neat, cm-1): 725, 1010 (Si-O), 1658 (C=O), 2972
1
(C=C-H). H NMR (400 MHz, CDCl3, 25°C): δ 0.59 (m, 2H, -SiCH2-), 1.14 (t, J = 7.0 Hz,
9H, -OCH2CH3), 1.95 (m, 2H, -CCH2C-), 2.29 (s, 3H, CH3), 3.73 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 4.29 (t, J = 7.1 Hz, 2H, -N3CH2-), 5.19 (s, 2H, -OCH2-), 7.13 (d, J = 7.5 Hz, 2H,
H9, H11), 7.30-7.34 (m, 2H, H2, H6), 7.39 (d, J = 15.6 Hz, 1H, Hα), 7.46 (d, J = 7.5 Hz, 2H,
H8, H12), 7.53-7.57 (m, 2H, H3, H4), 7.57 (s, 1H, Tz-H), 7.71 (d, J = 15.6 Hz, 1H, Hβ). 13C
NMR (101 MHz, CDCl3/DMSO, 25 °C): δ 7.2 (SiCH2), 16.7 (OCH2CH3), 22.5 (CCH2C),
23.8 (CH3) 50.5 (N3CH2), 56.5 (OCH2CH3), 60.1 (OCH2), 112.6 (C6), 118.0 (C2), 119.4,
141.1 (Tz-C), 119.6 (Cα), 122.5 (C4), 127.1 (C8, C12), 128.0 (C9, C11), 128.2 (C3), 130.4
(C7), 137.8 (C10), 139.2 (C5), 142.8 (Cβ), 156.9 (C1), 187.5 (C=O).
(E)-1-(2-((1-(3-(triethoxysilyl)propyl)-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-3-(4-chloro
phenyl)prop-2-en-1-one (8u) The quantities used were as 7u (1.0 g, 3.4 mmol), AzPTES
(0.83 g, 3.4 mmol). Brown oil, Yield: 1.63 g, 89 %. Anal. Calcd. for C27H34ClN3O5Si: C,
59.60; H, 6.30; N, 7.72. Found: C, 59.53; H, 6.23; N, 7.67. IR (neat, cm-1): 727, 1073 (Si-O),
1
1661 (C=O), 2973 (C=C-H). H NMR (400 MHz, CDCl3, 25°C): δ 0.61 (m, 2H, -SiCH2-),
1.22 (t, J = 7.0 Hz, 9H, -OCH2CH3), 2.04 (m, 2H, -CCH2C-), 3.81 (q, J = 7.0 Hz, 6H, -
OCH2CH3), 4.38 (t, J = 7.2 Hz, 2H, -N3CH2-), 5.29 (s, 2H, -OCH2-), 7.23 (d, J = 8.2 Hz, 1H,
H2), 7.34 (s, 1H, H6), 7.40 (d, J = 8.4 Hz, 2H, H9, H11), 7.44 (d, J = 8.2 Hz, 1H, H4), 7.49
(d, J = 15.7 Hz, 1H, Hα), 7.59 (d, J = 8.5 Hz, 2H, H8, H12), 7.63-7.70 (m, 2H, H3, Tz-H),
13
7.76 (d, J = 15.7 Hz, 1H, Hβ). C NMR (101 MHz, CDCl3, 25 °C): δ 7.5 (SiCH2), 18.3
(OCH2CH3), 24.2 (CCH2C), 52.6 (N3CH2), 58.6 (OCH2CH3), 62.2 (OCH2), 114.3 (C6),
19

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119.8 (C2), 121.5, 139.5 (Tz-C), 122.4 (Cα), 122.9 (C4), 128.5 (C8, C12), 128.6 (C9, C11),
129.3 (C3), 129.7 (C7), 133.4 (C10), 136.5 (C5), 143.4 (Cβ), 158.6 (C1), 189.8 (C=O).
3. Results and Discussion
3.1 Synthesis
For the synthesis of variously substituted acetylinic chalcones, of the many methods
available, the most widely used method is the base catalyzed Claisen–Schmidt reaction.
Commercially available hydroxyacetophenones were subjected to O-alkylation with
propargyl bromide in the presence of K2CO3 in DMF. The intermediate acetylenes 4-6 were
obtained in excellent to quantitative yields which were then subjected to aldol condensation
with differently substituted aldehydes in the presence of methanolic NaOH resulting into
acetylinic chalcones 7a-7u in quite high yields. The solid chalcones were purified by
recrystallization (7a-7g,7l-7u) while the liquid products (7h-7k) were purified by column
chromatography.
These acetylinic chalcones were then clicked onto 3-azidopropyltriethoxysilane (3-
AzPTES) in THF/Et3N solvent system at 65 °C with the catalyst loading of Cu catalyst
[CuBr(PPh3)3] to afford 1,2,3-triazole encapped triethoxysilanes 8a-8u (Scheme 1, Table 1)
in excellent yields of 88-93%. All the newly synthesized compounds were well characterized
1
13
by IR, H and C NMR spectroscopy. All the silanes were synthesized under dry nitrogen
atmosphere using a vacuum glass line.
3.2 Characterization
The IR spectra of the newly synthesized compounds were recorded in the range of 4000-400
cm-1. The absorption frequencies were tuned to be in agreement with the structure of the
prepared compounds. All the compounds show strong absorption bands in the range of 1670-
20

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1649 cm-1, typical of C=O stretching vibrations of carbonyl bond. The blank region around
2100 cm-1 and 3300 cm-1 in silanes 8a-8u confirms the cyclisation of alkynyl moiety into
triazole unit. Moreover, stretching vibrations of C=CH of the triazole ring in the range of
2975-2964 cm-1 adds on to the evidence of cycloaddition. Furthermore, Si-O stretching
vibrations appear in all the silanes in the range of 785-722 cm-1 and 1095-1072 cm-1.
Multinuclear (1H and 13C) NMR spectra are well consistent with the structure of the
synthesized compounds. Doublets around 7.18-7.64 ppm and 7.46-8.13 ppm appear in the
NMR spectra of all the compounds corresponding to vinyl hydrogen atoms, α and β
respectively with a high J value of around 15 Hz confirming the (E)-configuration of the
chalcones. In the NMR spectra of acetylinic chalcones (7a-7u), alkynyl proton appears
around δ ≈ 2.4 ppm that upon cyclisation with 3-AzPTES shows a shift to δ = 7.3-7.7 ppm
(8a-8u) validating the cyclisation of alkynyl moiety into triazole unit. Additionally, shifting
of -OCH2 protons of acetylene group from δ = 4.7 ppm (7a-7u) to δ ≈ 5.2 ppm (8a-8u)
certifies the formation of cyclised product. Triplet at δ = 1.1-1.2 ppm and quartet at δ = 3.7-
3.8 ppm affirms the presence of triethoxysilyl group. Parallel shifting is observed in the
carbon spectrum of the respective compounds.
13
In C NMR spectra of all compounds, the carbonyl carbon appears as the least shielded
carbon in the region δ = 187.5-192.8 ppm. Two carbons of alkynyl moiety (7a-7u) appear in
the range of δ = 76.0-78.8 ppm that shift around δ = 119.4-122.8 ppm and δ = 136.6-142.5
ppm in cyclised compounds (8a-8u), that confirms the cyclisation of alkyne functionality to
triazole unit. Carbon attached to silicon appears as the most shielded carbon at δ = 7.0-8.9
ppm for triethoxysilanes.
3.3 Photo-physical Properties
The UV-Vis absorption and emission spectra of triethoxysilanes were recorded in chloroform
at room temperature with the compound concentration of 10-6 M. The absorption maxima,
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molar extinction coefficient and emission maxima values are listed in Table 2. The effect of
different substitutions on the λ value of the compounds is studied and explained on the basis
of electron donating and withdrawing effects of the substituents. Chalcones belong to the
class of intermolecular charge transfer compounds in which two phenyl rings are connected
through a conjugation bridge as shown in Figure 1. Functionalization of both ends of the
phenyl rings with appropriate electron donor and acceptor groups can enhance the
asymmetric electronic distribution. Thus, the photo-physical properties of these conjugate
intramolecular charge transfer compounds strongly depend on the nature of the substituent.
OTES 8a-8u bearing chalcone moieties strongly absorb in the region 300-400 nm as shown
in Figures 2-4. These absorption bands are probably due to п-п* transitions. Compounds
substituted with one methoxy group at ortho (8b,8i,8p) or para position (8c,8j,8q) of ring A
displayed a bathochromic shift as compared to the unsubstituted chalcones (8a,8h,8o).
Electron donating methoxy group with lone pair of electrons on the oxygen atom adjacent to
п-system activates the aromatic ring by increasing the electron density on the ring through a
resonance donating effect thus resulting in the shifting of absorption band to the longer
wavelength. This effect increases as the number of methoxy groups is increased to two in
8d,8k and 8r. However, on the introduction of the third methoxy group at the meta position
of ring A (8e,8l,8s), the absorbance value was decreased due to diminished contribution of
the substituent towards resonance. In addition, the third methoxy group provides some stearic
hindrance resulting into conformational disorder. With the methyl group at para position of
ring A (8f,8m,8t), only a small bathochromic shift was observed. This is understandable on
the basis of hyper-conjugation effect of this group. Halogen substituents are a little unusual in
that they are both inductive electron withdrawing and resonance donating because of lone
pair of electrons. Therefore, the presence of 4-chloro functionality on ring A (8g,8n,8u)
resulted into a trivial hypsochromic shift as compared to methyl substituents. However, a
22

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small bathochromic shift as compared to the unsubstituted compounds can be rationalized in
terms of more dominating electron releasing effect.
Fluorescence spectral data of all the compounds were presented as emission spectra.
Emission spectra vary widely and are dependent upon the chemical structure of the
fluorophore. A fluorophore absorbs a photon of light to reach an energetically excited state
from where it deactivates to return to the ground state. The fate of this species depends upon
the exact nature of the fluorophore. In general, electron withdrawing group will decrease the
fluorescence property. On the contrary, electron donating group will enhance this property.
All the spectra were recorded in chloroform as solvent by giving an excitation in the range of
360-400 nm. All the compounds show good fluorescence behaviour and their emission
spectra present maxima wavelength in the range of 432-525 nm as shown in Figures 5-7. The
fluorescence of the compounds with unsubstituted ring A shows the shortest emission
wavelength but this wavelength increases as the number of electron donating methoxy
substituents increase. As the electron donating tendency of the methyl substituent is less in
comparison to the methoxy substituent, so compounds with methyl substitution emit at a
comparatively shorter wavelength. The chloro substituted compounds show blue shift in
comparison to tri-methoxy substituents but they exhibit a red shift of fluorescence maximum
as compared to the unsubstituted OTES. This shows the participation of the lone pair of
electrons of the chlorine atom thus establishing its role as a donor through the resonance
effect.
4. Conclusion
An efficient and simple protocol of ‘Click Silylation’ is pursued for the synthesis of OTES
functionalized with biologically potent chalcones. The assembly of different organic moieties
into a single framework results into hybrid biomaterials that can be put to further applications
23

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in diverse fields. The photo-physical properties of OTES were evaluated and the effect of
different substitutions was studied. The outcome of various substituents is concluded by the
observation that the silanes with electron donating substituents absorbed at longer wavelength
than the ones with electron withdrawing groups.
List of abbreviations
AzPTES: 3-azidopropyltriethoxysilane, OTES: Organotriethoxysilanes, CuAAC: Copper
catalysed Azide Alkyne Cycloaddition, NLO: non-linear optical
Acknowledgement
The authors would like to thank CSIR, New Delhi for providing financial support. Special
thanks to Mr. Avtar Singh, SAIF, Panjab University, Chandigarh for NMR studies.
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