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Non-symmetric benzo[b]-fused BODIPYs as a versatile fluorophore platform reaching the NIR: a systematic study of the underlying structure-property relationship
被引:23
作者:

Bessette, Andre
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Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada
PCAS Canada Inc, 725 Trotter St, St Jean, PQ J3B 8J8, Canada Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada

Auvray, Thomas
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Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada

Desilets, Denis
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PCAS Canada Inc, 725 Trotter St, St Jean, PQ J3B 8J8, Canada Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada

Hanan, Garry S.
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Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada
机构:
[1] Univ Montreal, Dept Chem, Pavillon J-A Bombardier,5155 Decelles Ave, Montreal, PQ H3T 2B1, Canada
[2] PCAS Canada Inc, 725 Trotter St, St Jean, PQ J3B 8J8, Canada
基金:
加拿大自然科学与工程研究理事会;
关键词:
ORGANIC SOLAR-CELLS;
TUNABLE FLUORESCENT DYES;
NON-FULLERENE ACCEPTORS;
LARGE STOKES SHIFT;
C-H ARYLATION;
FUSED BODIPY;
TRIPLET PHOTOSENSITIZERS;
FACILE SYNTHESIS;
RATIONAL DESIGN;
SINGLET OXYGEN;
D O I:
10.1039/c5dt04444h
中图分类号:
O61 [无机化学];
学科分类号:
070301 ;
081704 ;
摘要:
Ten newly synthesized non-symmetric benzo[b]-fused BODIPYs are compared with an extended series of nine related families (23 compounds) to gain insights into their structure-property relationship. The insertion of a fused indole moiety into the dipyrromethene core and various substituents on the proximal aryl including fused aromatic groups, lead to pronounced changes in the properties of compounds 1-10. By taking advantage of this versatile synthetic platform that allows facile substituent modifications and extension of the pi-conjugated system, significant bathochromic shifts in the absorption (lambda(max) = 511-597 nm) and emission (601-757 nm) bands are achieved. Although the oxidation potentials of the compounds vary considerably throughout the series (+1.28-+1.65 V) due to the significant contribution of the aryl function to the HOMO, the reduction remains much more consistent (-0.61 to -0.79 V) as the LUMO resides primarily on the dipyrromethene core with little aryl contribution as calculated by DFT. For example, installation of a dimethylamine substituent in the para position of the aryl group leads to drastic modification of the optoelectronic properties of the absorption (597 nm) and emission (757 nm) maxima. The full electrochemical, photophysical and computational analyses of the compounds along with the structural characterization of compounds 1, 5, 8, and 9 are used to rationalize the potential of this powerful platform.
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页码:7589 / 7604
页数:16
相关论文
共 99 条
[31]
Accurate Simulation of Optical Properties in Dyes
[J].
Jacquemin, Denis
;
Perpete, Eric A.
;
Ciofini, Ilaria
;
Adamo, Carlo
.
ACCOUNTS OF CHEMICAL RESEARCH,
2009, 42 (02)
:326-334

Jacquemin, Denis
论文数: 0 引用数: 0
h-index: 0
机构:
Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium

Perpete, Eric A.
论文数: 0 引用数: 0
h-index: 0
机构:
Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium

Ciofini, Ilaria
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Natl Super Chim Paris, CNRS UMR 7575, Lab Electrochim & Chim Analyt, F-75231 Paris, France Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium

Adamo, Carlo
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Natl Super Chim Paris, CNRS UMR 7575, Lab Electrochim & Chim Analyt, F-75231 Paris, France Fac Univ Notre Dame Paix, Lab Chim Theor Appliquee, B-5000 Namur, Belgium
[32]
Synthesis and Functionalization of Asymmetrical Benzo-Fused BODIPY Dyes
[J].
Jiao, Lijuan
;
Yu, Changjiang
;
Liu, Mingming
;
Wu, Yangchun
;
Cong, Kebing
;
Meng, Ting
;
Wang, Yuqing
;
Hao, Erhong
.
JOURNAL OF ORGANIC CHEMISTRY,
2010, 75 (17)
:6035-6038

Jiao, Lijuan
论文数: 0 引用数: 0
h-index: 0
机构:
Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Yu, Changjiang
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Liu, Mingming
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Wu, Yangchun
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Cong, Kebing
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Meng, Ting
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Wang, Yuqing
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China

Hao, Erhong
论文数: 0 引用数: 0
h-index: 0
机构: Anhui Normal Univ, Coll Chem & Mat Sci, Anhui Key Lab Funct Mol Solids, Wuhu 241000, Peoples R China
[33]
Direct synthesis of aryl substituted pyrroles from calcium carbide: an underestimated chemical feedstock
[J].
Kaewchangwat, Narongpol
;
Sukato, Rangsarit
;
Vchirawongkwin, Viwat
;
Vilaivan, Tirayut
;
Sukwattanasinitt, Mongkol
;
Wacharasindhu, Sumrit
.
GREEN CHEMISTRY,
2015, 17 (01)
:460-465

Kaewchangwat, Narongpol
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand

Sukato, Rangsarit
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand

Vchirawongkwin, Viwat
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Fac Sci, Dept Chem, Bangkok 10330, Thailand Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand

论文数: 引用数:
h-index:
机构:

Sukwattanasinitt, Mongkol
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Dept Chem, Fac Sci, Nanotec CU Ctr Excellence Food & Agr, Bangkok 10330, Thailand Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand

Wacharasindhu, Sumrit
论文数: 0 引用数: 0
h-index: 0
机构:
Chulalongkorn Univ, Dept Chem, Fac Sci, Nanotec CU Ctr Excellence Food & Agr, Bangkok 10330, Thailand Chulalongkorn Univ, Program Petrochem & Polymer Sci, Fac Sci, Bangkok 10330, Thailand
[34]
BODIPY dyes in photodynamic therapy
[J].
Kamkaew, Anyanee
;
Lim, Siang Hui
;
Lee, Hong Boon
;
Kiew, Lik Voon
;
Chung, Lip Yong
;
Burgess, Kevin
.
CHEMICAL SOCIETY REVIEWS,
2013, 42 (01)
:77-88

Kamkaew, Anyanee
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA

Lim, Siang Hui
论文数: 0 引用数: 0
h-index: 0
机构:
Subang Jaya Med Ctr, Canc Res Initiat Fdn CARIF, Subang Jaya 47500, Selangor, Malaysia
Univ Malaya, Fac Med, Dept Pharm, Kuala Lumpur 50603, Malaysia Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA

Lee, Hong Boon
论文数: 0 引用数: 0
h-index: 0
机构:
Subang Jaya Med Ctr, Canc Res Initiat Fdn CARIF, Subang Jaya 47500, Selangor, Malaysia Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA

Kiew, Lik Voon
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Malaya, Fac Med, Dept Pharmacol, Kuala Lumpur 50603, Malaysia Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA

Chung, Lip Yong
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Malaya, Fac Med, Dept Pharm, Kuala Lumpur 50603, Malaysia Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA

Burgess, Kevin
论文数: 0 引用数: 0
h-index: 0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA Texas A&M Univ, Dept Chem, College Stn, TX 77841 USA
[35]
Structural control of the photodynamics of boron-dipyrrin complexes
[J].
Kee, HL
;
Kirmaier, C
;
Yu, LH
;
Thamyongkit, P
;
Youngblood, WJ
;
Calder, ME
;
Ramos, L
;
Noll, BC
;
Bocian, DF
;
Scheidt, WR
;
Birge, RR
;
Lindsey, JS
;
Holten, D
.
JOURNAL OF PHYSICAL CHEMISTRY B,
2005, 109 (43)
:20433-20443

Kee, HL
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Kirmaier, C
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Yu, LH
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Thamyongkit, P
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Youngblood, WJ
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Calder, ME
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Ramos, L
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Noll, BC
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Bocian, DF
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Scheidt, WR
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Birge, RR
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Lindsey, JS
论文数: 0 引用数: 0
h-index: 0
机构: Washington Univ, Dept Chem, St Louis, MO 63130 USA

Holten, D
论文数: 0 引用数: 0
h-index: 0
机构:
Washington Univ, Dept Chem, St Louis, MO 63130 USA Washington Univ, Dept Chem, St Louis, MO 63130 USA
[36]
Optimization of distyryl-Bodipy chromophores for efficient panchromatic sensitization in dye sensitized solar cells
[J].
Kolemen, Safacan
;
Bozdemir, O. Altan
;
Cakmak, Yusuf
;
Barin, Gokhan
;
Erten-Ela, Sule
;
Marszalek, Magdalena
;
Yum, Jun-Ho
;
Zakeeruddin, Shaik M.
;
Nazeeruddin, Mohammad K.
;
Graetzel, Michael
;
Akkaya, Engin U.
.
CHEMICAL SCIENCE,
2011, 2 (05)
:949-954

Kolemen, Safacan
论文数: 0 引用数: 0
h-index: 0
机构:
Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Bozdemir, O. Altan
论文数: 0 引用数: 0
h-index: 0
机构:
Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Cakmak, Yusuf
论文数: 0 引用数: 0
h-index: 0
机构:
Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Barin, Gokhan
论文数: 0 引用数: 0
h-index: 0
机构:
Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Erten-Ela, Sule
论文数: 0 引用数: 0
h-index: 0
机构:
Ege Univ, Inst Solar Energy, TR-35100 Izmir, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Marszalek, Magdalena
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Yum, Jun-Ho
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Zakeeruddin, Shaik M.
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Nazeeruddin, Mohammad K.
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Graetzel, Michael
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Photon & Interfaces, CH-1015 Lausanne, Switzerland Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey

Akkaya, Engin U.
论文数: 0 引用数: 0
h-index: 0
机构:
Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey
Bilkent Univ, Dept Chem, TR-06800 Ankara, Turkey Bilkent Univ, UNAM Inst Mat Sci & Nanotechnol, TR-06800 Ankara, Turkey
[37]
BODIPY-based probes for the fluorescence imaging of biomolecules in living cells
[J].
Kowada, Toshiyuki
;
Maeda, Hiroki
;
Kikuchi, Kazuya
.
CHEMICAL SOCIETY REVIEWS,
2015, 44 (14)
:4953-4972

Kowada, Toshiyuki
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Immunol Frontier Res Ctr IFReC, Suita, Osaka 5650871, Japan Osaka Univ, Immunol Frontier Res Ctr IFReC, Suita, Osaka 5650871, Japan

Maeda, Hiroki
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan Osaka Univ, Immunol Frontier Res Ctr IFReC, Suita, Osaka 5650871, Japan

Kikuchi, Kazuya
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Immunol Frontier Res Ctr IFReC, Suita, Osaka 5650871, Japan
Osaka Univ, Grad Sch Engn, Suita, Osaka 5650871, Japan Osaka Univ, Immunol Frontier Res Ctr IFReC, Suita, Osaka 5650871, Japan
[38]
Boron-dibenzopyrromethene-based organic dyes for application in dye-sensitized solar cells
[J].
Kubo, Yuji
;
Eguchi, Daichi
;
Matsumoto, Asaki
;
Nishiyabu, Ryuhei
;
Yakushiji, Hidenori
;
Shigaki, Koichiro
;
Kaneko, Masayoshi
.
JOURNAL OF MATERIALS CHEMISTRY A,
2014, 2 (15)
:5204-5211

Kubo, Yuji
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

Eguchi, Daichi
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

Matsumoto, Asaki
论文数: 0 引用数: 0
h-index: 0
机构:
Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

论文数: 引用数:
h-index:
机构:

Yakushiji, Hidenori
论文数: 0 引用数: 0
h-index: 0
机构:
Nippon Kayaku Co Ltd, Kita Ku, Tokyo 1158588, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

Shigaki, Koichiro
论文数: 0 引用数: 0
h-index: 0
机构:
Nippon Kayaku Co Ltd, Kita Ku, Tokyo 1158588, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan

Kaneko, Masayoshi
论文数: 0 引用数: 0
h-index: 0
机构:
Nippon Kayaku Co Ltd, Kita Ku, Tokyo 1158588, Japan Tokyo Metropolitan Univ, Grad Sch Urban Environm Sci, Dept Appl Chem, Hachioji, Tokyo 1920397, Japan
[39]
Halogenated boron-dipyrromethenes: synthesis, properties and applications
[J].
Lakshmi, Vellanki
;
Rao, Matakalapalli Rajeswara
;
Ravikanth, Mangalampalli
.
ORGANIC & BIOMOLECULAR CHEMISTRY,
2015, 13 (09)
:2501-2517

Lakshmi, Vellanki
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

Rao, Matakalapalli Rajeswara
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

Ravikanth, Mangalampalli
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
[40]
Synthesis and Properties of Meso-unsubstituted 3-Pyrrolyl Boron Dipyrromethene
[J].
Lakshmi, Vellanki
;
Shaikh, Mushtaque S.
;
Ravikanth, Mangalampalli
.
JOURNAL OF FLUORESCENCE,
2013, 23 (03)
:519-525

Lakshmi, Vellanki
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

Shaikh, Mushtaque S.
论文数: 0 引用数: 0
h-index: 0
机构:
Bombay Coll Pharm, Dept Pharmaceut Chem, Mumbai 400098, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

Ravikanth, Mangalampalli
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India