Mangalampalli Ravikanth

Indian Institute of Technology Bombay, Mumbai, Maharashtra, India

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Publications (173)559.58 Total impact

  • [Show abstract] [Hide abstract]
    ABSTRACT: Herein, we report synthesis, separation and characterisation of E- and Z-isomers of dipyrrolyldiphenylethene to study their emission behaviour in aggregation state and solid state. E-isomer showed pronounced Aggregation Induced Emission (AIE) whereas Z-isomer showed Crystallization Induced Emission (CIE). Present study explains that emission behaviour (AIE/CIE) is dependent on the inter/intra molecular interactions between the molecules. The study also validates that Restriction of Intramolecular Rotation (RIR) is the main cause of AIE/CIE in olefinic luminogens (TPE type of systems) rather than E/Z isomerisation.
    Physical Chemistry Chemical Physics 06/2015; DOI:10.1039/C5CP02400E · 4.20 Impact Factor
  • The Journal of Physical Chemistry C 04/2015; 119(15):8095-8102. DOI:10.1021/acs.jpcc.5b02712 · 4.84 Impact Factor
  • Hemanta Kalita, Mangalampalli Ravikanth
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    ABSTRACT: Novel boron-dipyrromethene (BODIPY)-bridged 22-oxacorrole dyads, using meso-pyrrolyl 22-oxacorrole as a key synthon, have been synthesized. The reactivity of the meso-pyrrolyl group of 22-oxacorrole was exploited to synthesize the first examples of BODIPY-bridged 22-oxacorrole dyads in ≈40 % yield. The dyads are stable and exhibited interesting spectral and electrochemical properties. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Chemistry - A European Journal 04/2015; 21(20). DOI:10.1002/chem.201500702 · 5.70 Impact Factor
  • Mangalampalli Ravikanth, Emandi Ganapathi, Tamal Chatterjee, Way-Zen Lee
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    ABSTRACT: Our successful synthesis of first examples of nonaromatic 24 core-modified pentaphyrins containing six meso carbons is reported.The core-modified pentaphyrins containing six meso carbons were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol)with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions.By this methodology, we obtained two stable core-modified pentaphyrins containing six meso carbons in decent yields.The core-modified pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques and also by X-ray crystallography for one of the pentaphyrin macrocycle.The crystal structure revealed that the macrocycles is almost planar and one of the thiophene rings which is positioned opposite to the ethene bridged meso-carbons is inverted.Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ion.
    Asian Journal of Organic Chemistry 04/2015; DOI:10.1002/ajoc.201500072 · 2.29 Impact Factor
  • Tejinder Kaur, Tamanna K. Khan, Mangalampalli Ravikanth
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    ABSTRACT: Cyclotriphosphazene and cyclotetraphosphazene appended with six and eight sapphyrin units, respectively, were prepared by treating N3P3Cl6 and N4P4Cl8 with the appropriate equivalents of 5,10,15-tri(p-tolyl)-20-(4-hydroxyphenyl)-25,27,29-trithiasapphyrin in tetrahydrofuran (THF) in the presence of Cs2CO3 at temperatures of 0 to 60 °C for 8–12 h. The two multi-expanded porphyrin assemblies were soluble in common organic solvents, and their identities were confirmed by their corresponding molecular ion peak in the MALDI-TOF mass spectra. 1D and 2D NMR spectroscopic techniques were used to deduce the molecular structures of the mult-expanded porphyrin assemblies. Absorption spectral studies showed that the band positions of the multisapphyrin assemblies were similar to that of the monomeric sapphyrin, but the extinction coefficients were three- to fourfold higher than that of the monomeric sapphyrin. The multisapphyrin assemblies are not very stable under redox conditions.
    European Journal of Organic Chemistry 03/2015; 2015(14). DOI:10.1002/ejoc.201500131 · 3.15 Impact Factor
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    ABSTRACT: Miniaturization of integrated circuits is happening at a rapid pace since the last two decades. Physical limits are beginning to saturate the growth of Si-CMOS technology and have prompted technologists to look for alternative approaches for miniaturization. Molecular Electronics is proving to be a viable option to fabricating high-density circuits, leveraging properties of organic molecules. Carbon nanotubes, polyphenylenes, porphyrins and DNA strands are some of the molecules that are being actively researched upon. In this article the current status of research in the area of molecular electronics is reviewed, and the roadblocks identified using an extensive database of research in this area. The current research efforts in the area of molecular electronics at IIT Bombay are also briefly discussed.
    IETE Technical Review 03/2015; 19(5):307-315. DOI:10.1080/02564602.2002.11417045 · 0.93 Impact Factor
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    Tamal Chatterjee, Sivaiah Areti, Mangalampalli Ravikanth
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    ABSTRACT: The first stable calixazasmaragdyrins containing two meso-sp(2) and one meso-sp(3) carbon atoms were synthesized by [3 + 2] condensation of 2,2'-(1-methylethylidene)bis(pyrrole) and 5,10-diaryltripyrromethane under trifluoroacetic acid catalyzed conditions. The macrocycles were confirmed by high-resolution mass spectrometry, and the molecular structures were deduced by detailed 1D and 2D NMR spectroscopy. The single-crystal structural analysis showed the highly strained and distorted nature of a calixazasmaragdyrin macrocycle. The presence of the one meso-sp(3) carbon center induces sufficient flexibility into the macrocycle, which, in turn, helps with the stability of the calixazasmaragdyrin macrocycle. The calixazasmargdyrins showed one broad absorption band at ∼425 nm and an ill-defined band at ∼685 nm. The electrochemical studies revealed that the calixazasmaragdyrins are not stable under redox conditions. Because the calixazasmargdyrin macrocycle possesses five pyrrole rings with three ionizable inner NH protons, we investigated anion and cation sensing properties of calixazasmargdyrins. Our studies revealed that the calixazasmaragdyrins do not show any sensing behavior toward anions but exhibited specific sensing behavior toward Hg(2+) ions as verified by spectral and electrochemical studies.
    Inorganic Chemistry 03/2015; 54(6). DOI:10.1021/ic503028k · 4.79 Impact Factor
  • A. Dvivedi, P. Rajakannu, M. Ravikanth
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    ABSTRACT: The meso-salicylaldehyde substituted BODIPY was synthesized over sequence of steps and characterized by X-ray crystallography, mass, NMR, absorption, fluorescence and electrochemical techniques. The crystal structure showed the presence of strong intramolecular hydrogen bonding between hydroxyl and formyl group which induces rigidity in the BODIPY core and makes the BODIPY relatively more fluorescent compared to meso-phenyl BODIPY. Our studies showed that the meso-salicyaldehyde BODIPY can be used as specific chemidosimetric sensor for CN- ion. The presence of hydroxyl group adjacent to formyl group helps in activating the formyl group for nucleophilic attack. Upon addition of CN- ion to meso-salicylaldehyde BODIPY, the CN- ion attacks the formyl group and converts to cyanohydrin group. This irreversible reaction was monitored by following the changes in absorption, fluorescence and electrochemical properties and the results support that meso-salicylaldehyde substituted BODIPY can be used as specific chemodosimetric sensor for CN- ion. To substantiate the role of hydroxyl group, we also prepared meso(m-formylphenyl) BODIPY which contains only formyl group on meso-phenyl and our studies indicated that meso(m-formylphenyl) BODIPY cannot be used as chemodosimetric sensor for CN- ion, as verified by absorption and emission studies.
    Dalton Transactions 01/2015; · 4.10 Impact Factor
  • Emandi Ganapathi, Tamal Chatterjee, Mangalampalli Ravikanth
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    ABSTRACT: Expanded dithiacalixphyrins with the N2S2 core containing two sp(3) and three sp(2)meso-carbons have been prepared by condensation of one equivalent of butene-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with one equivalent of 5,5'-dialkyldipyrromethane under mild acid catalyzed conditions in decent yields. The expanded dithiacalixphyrins were characterized by HR-MS, 1D and 2D NMR techniques and the structure of one of the expanded dithiacalixphyrin macrocycles was solved by X-ray crystallography. The crystal structure analysis indicated that the macrocycle is highly distorted and attains a boat shaped structure. The expanded thiacalixphyrins showed a specific sensing ability for F(-) ions over other anions as judged from absorption, NMR and mass spectral studies.
    Dalton Transactions 12/2014; 44(6). DOI:10.1039/c4dt03215b · 4.10 Impact Factor
  • Sunit Kumar, Mangalampalli Ravikanth
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    ABSTRACT: A series of functionalized meso-boron dipyrromethenyl porphyrin building blocks were synthesized by condensing one equivalent of readily available 2-formyl boron dipyrromethene (2-formyl BODIPY) with two equivalents of meso-anisyl dipyrromethane and one equivalent of functionalized aldehyde under mild acid catalyzed conditions followed by column chromatographic purification and afforded in 5–7% yields. The meso-BODIPYnyl porphyrins are freely soluble in common organic solvents and characterized by mass, spectral and electrochemical techniques. The presence of a BODIPY unit directly at the meso-position alters the π-delocalization of the porphyrin macrocycle. The compounds are weakly fluorescent because of effective charge transfer between the porphyrin and BODIPY units leading to the formation of a low lying charge transfer state. The meso-BODIPYnyl porphyrin–BF2–smaragdyrin conjugate was synthesized by coupling a meso-BODIPYnyl porphyrin building block containing a meso-iodophenyl group with ethynyl BF2–smaragdyrin under Pd(0) coupling conditions. The spectral and electrochemical studies indicated that the photo-induced electron transfer is the predominant process in the meso-BODIPYnyl porphyrin–BF2–smaragdyrin conjugate.
    RSC Advances 11/2014; 4(109). DOI:10.1039/C4RA10807H · 3.71 Impact Factor
  • Tejinder Kaur, Malakalapalli Rajeswararao, Mangalampalli Ravikanth
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    ABSTRACT: We report the synthesis of first examples of hexaporphyrin and dodecaporphyrin assemblies on cyclotriphosphazene scaffold by adopting two different approaches based on Ru-pyridyl "N" coordination in decent yields. The multiporphyrin assemblies were confirmed by (31)P, (13)C, (1)H, (1)H-(1)H COSY, and NOESY NMR spectroscopic studies. The absorption studies showed 2-fold intensity enhancement with negligible changes in peak maxima compared to porphyrin monomers. The redox potentials of multiporphyrin assemblies showed the redox features of the constituted porphyrin monomers and supported weak interactions among the porphyrin units in noncovalent hexaporphyrin and dodecaporphyrin arrays.
    Inorganic Chemistry 10/2014; 53(20). DOI:10.1021/ic501569e · 4.79 Impact Factor
  • Emandi Ganapathi, Tamal Chatterjee, Mangalampalli Ravikanth
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    ABSTRACT: A simple route was developed for the synthesis of 9,10,19,20-tetraarylporphycenes by combining both McMurry and oxidative synthetic strategies and using readily available precursors. The desired 5,6-diaryldipyrroethenes, which were prepared in multigram quantities over two steps, were used to prepare 9,10,19,20-tetraarylporphycenes under mild acid-catalyzed conditions. As 5,6-diaryldipyrroethene precursors can easily be prepared in multigram quantities, this method is useful for the preparation of meso-tetrarylporphycenes that contain different aryl substituents. The molecular structures of these macrocycles were determined by HRMS analysis as well as 1D and 2D NMR studies. The tetraarylporphycenes exhibited a strong Soret band at approximately 380 nm and three Q bands in the region of 580–655 nm. The tetraarylprophycenes are reasonably fluorescent and stable under redox conditions.
    European Journal of Organic Chemistry 10/2014; 2014(30). DOI:10.1002/ejoc.201402770 · 3.15 Impact Factor
  • Tamal Chatterjee, Mangalampalli Ravikanth
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    ABSTRACT: The palladium(II) complex of calixoxasmaragdyrin was prepared in 80% yield by treating the free base calixoxasmaragdyrin with PdCl2 in CH3CN at reflux temperature. The crystal structure solved for Pd(II) calixoxasmaragdyrin indicates that the calixoxasmaragdyrin macrocycle is highly distorted and attained a boat shaped structure. The Pd(II) ion is coordinated to four pyrrolic nitrogens in square planar fashion, and it is placed at ∼0.138 Å above from the four coordinating pyrrole nitrogens plane (N1N2N3N4). The Pd-N bond lengths are inequivalent, and the Pd(II) ion is positioned more toward the dipyrromethane moiety of calixoxasmaragdyrin. The complex shows one broad absorption band at 477 nm and is not very stable under redox conditions. The Pd(II) calixoxasmaragdyrin showed good catalytic activity in the Suzuki-Miyaura cross coupling reactions.
    Inorganic Chemistry 09/2014; 53(19). DOI:10.1021/ic501595f · 4.79 Impact Factor
  • Emandi Ganapathi, Way-Zen Lee, Mangalampalli Ravikanth
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    ABSTRACT: The stable non-aromatic [20]dithiaporphyrin (2.1.1.1) macrocycles were synthesized in decent yields by condensing readily available butene-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl dipyrromethanes under mild acid catalyzed conditions. The [20]dithiaporphyrin (2.1.1.1) macrocycles are the first member of expanded porphyrin analogue of [18]dithiaporphyrin (1.1.1.1) and consists two pyrroles and two thiophenes connected through five meso carbon bridges. The [20]dithiaporphyrin macrocycles were confirmed by mass, 1D and 2D NMR and X-ray crystallography. The X-ray structure revealed that the macrocycle is highly distorted and the two thiophene rings are completely out-of-plane from the "mean-plane" defined by the dipyrromethene moiety and the two meso carbons. In absorption spectrum, the macrocycles showed one strong band at ~420 nm and one weak band at ~720 nm. The electrochemical studies revealed that the macrocycles are stable under redox conditions. The metal sensing studies indicated that these macrocycles have potential to sense specific metal ions such as Hg2+ ion. Two covalently linked dithiahomoporphyrin-fluorophore dyads were synthesized by coupling iodo-functionalized dithiahomoporphyrin with ethynyl functionalized fluorophore such as boron-dipyrromethene (BODIPY) and BF2-smaragdyrin under mild Pd(0) coupling conditions. The potential of these dyads as fluorescent sensor for Hg2+ was explored and the studies indicated that both dyads can be used as fluorescent sensors.
    The Journal of Organic Chemistry 09/2014; 79(20). DOI:10.1021/jo501724d · 4.64 Impact Factor
  • Vellanki Lakshmi, Mangalampalli Ravikanth
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    ABSTRACT: A series of sterically crowded, mixed hexasubstituted BODIPYs containing two different types of substituents on the pyrrole carbons have been synthesized in high yields by a stepwise approach. The mixed BODIPYs were synthesized by bromination of BODIPYs followed by coupling with appropriate boronic acids under Suzuki coupling conditions. This approach has allowed the introduction of two different types of methyl/aryl substituents at the designated positions of the BODIPY core. All the hexasubstituted BODIPYs are readily soluble in common organic solvents and have been characterized by various spectral and electrochemical techniques. The spectral studies indicated that the presence of mixed methyl/aryl substituents on the BODIPY core significantly alters the electronic properties, and the electrochemical studies revealed that the BODIPYs are stable under redox conditions.
    European Journal of Organic Chemistry 09/2014; 2014(26). DOI:10.1002/ejoc.201402599 · 3.15 Impact Factor
  • Hemanta Kalita, Way-Zen Lee, Mangalampalli Ravikanth
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    ABSTRACT: The aromatic PO2 complexes of meso-triaryl-25-oxasmaragdyrins were synthesized by treating the free base 25-oxasmaragdyrins with POCl3 in toluene/triethylamine at refluxing temperature. The complexes are stable and characterized by X-ray and different spectroscopic techniques. In these complexes, the phosphorus(V) ion was bound to two pyrrolic nitrogen atoms of the smaragdyrin macrocycle and two oxygen atoms in tetrahedral geometry. The X-ray structure revealed that the smaragdyrin macrocycle showed significant distortion upon insertion of a PO2 unit, and the phosphorus atom lies 1.339 Å above the mean plane defined by three meso-carbon atoms of the macrocycle. These complexes absorb strongly in the visible region and are 2.5 times more strongly fluorescent than free base 25-oxasmaragdyrins. The smaragdyrin macrocycle becomes electron-deficient upon complexation with a PO2 unit because these complexes are easier to reduce but difficult to oxidize compared to free base smaragdyrins. We designed and synthesized a covalently linked BODIPY-PO2-smaragdyrin dyad and demonstrated efficient energy transfer from the BODIPY unit to the PO2-smaragdyrin unit.
    Inorganic Chemistry 08/2014; 53(17). DOI:10.1021/ic501629n · 4.79 Impact Factor
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    ABSTRACT: Unsymmetrical 22‐oxacorrole containing two aryl groups and one pyrrole group at the meso position was synthesized by condensing one equivalent of 16‐oxatripyrrane with one equivalent of meso aryl dipyromethane under mild acid‐catalyzed conditions followed by oxidation with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ). This [3+2] condensation approach was expected to yield meso‐free 25‐oxasmaragdyrin but unexpectedly afforded unsymmetrical meso‐pyrrole‐substituted 22‐oxacorrole. We demonstrated the versatility of the reaction by synthesizing four new meso‐pyrrole‐substituted 22‐oxacorroles. The reactivity of α‐position of meso‐pyrrole was tested by carrying out various functionalization reactions such as bromination, formylation, and nitration and obtained the functionalized meso‐pyrrole‐substituted 22‐oxacorroles in decent yields. The X‐ray structure obtained for one of the functionalized meso‐pyrrole substituted 22‐oxacorrole revealed that the macrocycle was nearly planar and the meso‐pyrrole was in the perpendicular orientation with respect to the macrocyclic plane. The meso‐pyrrole‐substituted 22‐oxacorroles absorb strongly in 400–700 nm region with one strong Soret band and four weak Q bands. The 22‐oxacorroles are strongly fluorescent and showed emission maxima at ≈650 nm with decent quantum yields and singlet‐state lifetimes. The 22‐oxacorroles are redox‐active and exhibited three irreversible oxidations and one or two reversible reduction(s). A preliminary biological study indicated that meso‐pyrrole corroles are biocompatible. Mastering ABCorroles: Syntheses of the first examples of stable fluorescent meso‐pyrrole‐substituted 22‐oxacorroles are described (see scheme; TFA=trifluoroacetic acid; DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). A preliminary biological study indicated that meso‐pyrrole corroles are biocompatible.
    Chemistry 08/2014; 20(33). DOI:10.1002/chem.201402710 · 5.70 Impact Factor
  • Yogita Pareek, M. Ravikanth
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    ABSTRACT: 21-Thiaporphyrins and 21,23-dithiaporphyrins resulting from the replacement of one and two pyrrole rings respectively, of tetrapyrrolic porphyrins possess singlet state energy levels which are lower than porphyrins and metalloporphyrins. This specific feature of thiaporphyrins is advantageous when thiaporphyrins are connected either covalently or non-covalently to porphyrins and metalloporphyrins for unidirectional flow of energy transfer/electron transfer. In recent times, the synthetic routes were developed for the synthesis of functionalized thiaporphyrin building blocks which were not accessible earlier. The functionalized thiaporphyrins have been used to synthesize several unsymmetrical thiaporphyrin-based arrays containing two or more different types of porphyrin subunits whose singlet state energy levels are arranged in a favourable way for the energy transfer/electron transfer. In this review, we describe different synthetic approaches being employed for the synthesis of functionalized thiaporphyrin building blocks and their use in the construction of several covalently and non-covalently linked thiaporphyrin-based multiporphyrin arrays ranging from dyads to octads. The photophysical studies are also described to show the possibility of singlet-singlet energy transfer from one porphyrin unit to another in some selected thiaporphyrin-based multiporphyrin arrays.
    ChemInform 07/2014; 45(28). DOI:10.1002/chin.201428275
  • Sheri Madhu, Sk Josimuddin, Mangalampalli Ravikanth
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    ABSTRACT: Boron-dipyrromethenes containing dithioacetal substituents at 3,5-positions, 3,5-bis(dithioacetal) BODIPYs 1 and 2, were synthesized by treating their corresponding 3,5-diformyl BODIPYs 3 and 4 with excess methyl thioglycolate under mild acid catalyzed reaction conditions. The spectral and electrochemical studies indicated that 3,5-bis(dithioacetal) BODIPYs are less electron deficient compared to 3,5-diformyl BODIPYs. Furthermore, dithioacetal functional groups are very useful for binding metal ions and our studies clearly showed that these dyes can act as selective chemodosimetric probes for the recognition of Hg(II) ions over various other metal ions. The sensing phenomenon employs unique and irreversible Hg(II) promoted deprotection of the dithioacetal groups to aldehyde groups which is clearly demonstrated by absorption, fluorescence, HR-MS and NMR studies. Competitive binding experiments demonstrate that BODIPY 1 can specifically detect Hg(II) ions even in the presence of various other metal ions.
    New Journal of Chemistry 07/2014; 38(8). DOI:10.1039/C4NJ00593G · 3.16 Impact Factor
  • Sheri Madhu, Vijaya Kumar Hinge, Mangalampalli Ravikanth
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    ABSTRACT: We synthesized the hexa-coordinated Re(I) bridged BODIPY dyad 1 in decent yield by thermal reaction of benzimidazole substituted BODIPY 2 with Re(CO)(5)Cl. The dyad 1 was characterized by H-1, C-13, B-11, F-19 NMR, ESI-MS, FTIR, UV-vis, and electrochemical techniques. In Re(I) bridged dyad 1, the Re(I) ion is hexa-coordinated and coordinates with nitrogen atoms of two benzimidazole units, three axial carbonyl ligands and one chloride atom. The presence of three carbonyl groups in dyad 1 was verified by C-13 NMR and IR spectroscopy. The absorption and steady-state fluorescence spectra of Re(I) bridged BODIPY dyad showed a slightly broad and hypsochromically shifted absorption and emission bands compared to BODIPY 2. The electrochemical studies indicated that, the Re(I) bridge BODIPY dyad 1 was easy to reduce compared to BODIPY 2 supporting the electron deficient nature dyad upon Re(I) ion binding. The molecular structure of dyad 1 was further elucidated by DFT computational studies.
    Journal of Porphyrins and Phthalocyanines 07/2014; 18(07):535-541. DOI:10.1142/S1088424614500266 · 1.36 Impact Factor

Publication Stats

1k Citations
559.58 Total Impact Points

Institutions

  • 2003–2015
    • Indian Institute of Technology Bombay
      • • Department of Chemistry
      • • Centre for Research in Nanotechnology and Science (CRNTS)
      Mumbai, Maharashtra, India
  • 2004–2014
    • Indian Institute of Technology Ropar
      • Department of Chemistry
      Rūpar, Punjab, India
  • 2000–2014
    • Institute of Chemical Technology, Mumbai
      • Department of Chemistry
      Mumbai, Mahārāshtra, India
    • Maharashtra Institute of Technology
      Poona, Maharashtra, India
  • 2008
    • Indian Institute of Chemical Technology
      Bhaganagar, Telangana, India
  • 1993–2006
    • Indian Institute of Technology Kanpur
      • Department of Chemistry
      Cawnpore, Uttar Pradesh, India
  • 1999
    • Kyoto University
      • Division of Chemistry
      Kioto, Kyōto, Japan
  • 1995–1997
    • Tata Institute of Fundamental Research
      • Department of Chemical Sciences
      Mumbai, Maharashtra, India
  • 1994
    • Uttar Pradesh Textile Technology Institute
      Cawnpore, Uttar Pradesh, India