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S

S
ER

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SW

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A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
b Inter system crossing (ISC)
S

S
process
ER

ER

ER
The molecule may also lose energy by another
SW

SW

SW
called inter system crossing (ISC). These transitions involve
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

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 SW

SW

SW
N

N
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E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER
SW

SW

SW
N

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A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
Photochemistry
3.47
the return of the activated molecules from the states of
different spins, ie., between singlet and triplet states.
S

S
ER

ER

ER
SW

SW

S2
S2 >T2 SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
S1 T
01

01

01
E2

E2

E2
EE

EE

EE
These transitions are forbidden, occurs relatively at
@

@
slow rates.
S

S
ER

ER

ER
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
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N
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E2

E2

E2
EE

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EE
@

@
S

S
ER

ER

ER
SW

SW

SW
N

N
(a) Internal conversion (IC)
A

A
the activated
EG

EG

EG
return of

E
the
These transitions involve states to the first excited
7R

7R

7R
01

01

01
excited
molecule from the higher
E2

E2

E2
EE

EE

EE
states, 1e.,
@

@
S3 S
S2 >S
S

S
ER

ER

ER
SW

SW

(or) SW
N

N
A

T
EG

EG

EG

T3

E
7R

7R

7R
01

01

01
E2

E2

E2
T2 T
EE

EE

EE
@

molecule is given out in @

The energy of the activated
This process
the form of heat through molecular collisions.
occurs in less than about
is called internal conversion (IC). It
S

S
ER

ER

ER

101 second.
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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EE

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@

@
S

S
ER

ER

ER
SW

SW

SW
(a) Fluorescence
N

N
A

A
EG

EG

EG
The emission of radiation due to the transition from

E
7R

7R

7R
singlet excited state, S to ground state So is called
01

01

01
E2

E2

E2
EE

EE

EE
fluorescence. This transition is allowed transition and occurs
@

@
in about 10 second.

SSo
S

S
ER

ER

ER
SW

SW

SW
N

N
A

(b) Phosphorescence
EG

EG

EG

E
7R

7R

7R
01

01

01
The emission of radiation due to the transition from
E2

E2

E2
the triplet excited state T to the ground state So is called
EE

EE

EE
@

phosphorescence. This transition is slow and forbidden @

transition.
S

T So
ER

ER

ER
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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3.8.1 Fluorescence

E2

E2

E2
EE

EE

EE
@

@
When a beam of light is allowed to fall on a substance
t gets excited and emits radiation with in short time (about
8
10 sec). Emision stops as soon as the incident radiation
S

S
ER

ER

ER
is cut off. This process is called fluorescence.
SW

SW

SW
N

N
The substance, which shows fluorescence is called
A

A
EG

EG

EG

E
fluorescent substance.
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
Fluorite (naturally occurring CaF2) petroleum,
organic dyes like eosin, fluorescein, ultramarine and vapours
S

S
ER

ER

ER
of Na, Hg and I2.
SW

SW

SW
N

N
A

A
EG

EG

EG

Types of fluorescence

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
1. Resonance fluorescence
@

@
If the excited atom emits radiation of the same
frequency, the process is known as resonance fluorescenc
S

S
ER

ER

ER

Example
SW

SW

SW
N

N
A

A
EG

EG

EG

exposed t0
When mnercury vapour at low pressure is expose
E
7R

7R

7R

excited.
radiation of wavelength 253.7 nm, it gets excl
01

01

01
E2

E2

E2

emits
Subsequently, when it returns to its ground state, it
EE

EE

EE
@

radiation of the same frequency, which it absorbel:

S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

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Common to all branches

N

N
A

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G

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SW

SW
N

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If the molecule is excited, due to
EE

EE

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the transfer of part
@

@
af excitation energy from the foreign substance,
it emits the
radiation of lower frequency,
the process is known as
sensitized fluorescence.
S

S
ER

ER

ER
SW

SW

SW
Example|
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
The vapours of mercury, sodium, etc.,
E2

E2

E2
EE

EE

EE
@

@
Mechanism of Fluorescence
S

S
ER

ER

ER
Moleculees have even number of electrons in the
SW

SW

SW
N

N
ground state (So) and are paired. When it absorbs light, one
A

A
EG

EG

EG

E
of the paired electrons moves to the higher energy states
7R

7R

7R
01

01

01
(excited states) (S1, S2, S3, etc.). From the excited state the
E2

E2

E2
EE

EE

EE
molecules returns to the ground state by the following
@

@
process.

(a) From the excited state, the molecules return to the first
S

S
ER

ER

ER

excited state (S) through Internal Conversion (IC).

SW

SW

SW
N

N
A

S3S
EG

EG

EG

E
7R

7R

7R
01

01

01

S2S1
E2

E2

E2
EE

EE

EE
@

(b) From the S state the molecules returns to the ground

state (So) by emiting radiation, called fluorescence.
S

SSo
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
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SW

SW
N

N
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E2

E2

E2
EE

EE

EE
@

@
IC
S2
S

S
IC
ER

ER

ER
SW

SW

SW
S-
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER
SW

SW

So SW
N

N
A

A
EG

EG

EG

Fig. 3.6 Jablonskei diagram for fluorescence

E
7R

7R

7R
01

01

01
E2

E2

E2
Quenching of fluorescence
EE

EE

EE
@

The fluorescence may be quenched (stopped), when u @

excited molecule collides with a normal molecule before
fluoresces. During quenching, the energy of the exCiteu
molecule gets transferred to the molecule with which
S

S
ER

ER

ER

collides. Quenching.occurs in two ways.

SW

SW

SW
N

N
A

(a) Internal quenching

EG

EG

EG

E
7R

7R

7R

Ouenching may also occur, when

the molecule changes
01

01

01

from the singlet exCited state to the triplet excited state. This
E2

E2

E2
EE

EE

EE

phenomenon is called internal quenching

@

(b) External quenching

Quenching may also occur from h addition
of an
S

which absorbs energy

external substance, CHEMISTRY - I from the excited
ER

ER

ER

CY6151 - externa
ENGINEERING exCite
phenomenon is called external
SW

SW

SW

molecule.
Common to all branchesThis quenching.
N

N
A

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G

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SW
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N
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E2

E2

E2
Phosphorescence
EE

EE

EE
3.8.2
@

@
fall on a substance,
When a beam of light 1s allowed to
gets excited and emits radiati for sometime. Emission
it
even after the incident radiation
S

S
ontinuous for some time
ER

ER

ER
COn
off. This process 1S called phosphorescence (or)
SW

SW

SW
is Cut
N

N
delayed fluorescence.
A

A
EG

EG

EG

E
7R

7R

7R
The substance, which shows phosphorescence is called
01

01

01
E2

E2

E2
phosphorescent substance.
EE

EE

EE
@

@
Examples

ZnS, alkaline earth sulphides and sulphates of Ca, Ba

S

S
& Sr.
ER

ER

ER
SW

SW

SW
N

N
Mechanism of phosphorescence
A

A
EG

EG

EG

E
When a molecule absorbs light, one of its paired
7R

7R

7R
01

01

01
(S%) to the higher
electrons moves from the ground state
E2

E2

E2
EE

EE

EE
energy states (excited states) (S1, S2, S3, etc.)
@

@
return to the
From the excited state the molecules
process.
ground state by the following
S

S
ER

ER

ER

excited state to
(a) The molecule crosses from the singlet
SW

SW

SW

exCited states through Inter

the corresponding triplet
N

N
A

System Crossing (ISC).

EG

EG

EG

E
7R

7R

7R

t S3
01

01

01
E2

E2

E2
EE

EE

EE

S2 T2
@

S
T
excited state,
(b)
(D) From the triplet the molecule returns to
S

triplet excited state through

the first
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I Internal

Conversion (IC)
SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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E2

E2

E2
EE

EE

EE
@

@
Engineering Chemistry
3.52
T3 T
S

S
ER

ER

ER
SW

SW

SW
T2 >T
N

N
A

A
EG

EG

EG

E
From the T state, the molecule returns to the ground
7R

7R

7R
(c)
01

01

01
E2

E2

E2
state (So) by emitting radiation, called
EE

EE

EE
@

@
phosphorescence.

T
S

S
ER

ER

ER
IC
SW

SW

T2 SW
N

N
A

A
EG

EG

EG

E
IC
7R

7R

7R
T
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01

So
E2

E2

E2
EE

EE

EE

Fig, 3.7 Jablonski diagram

@

for phosphorescence
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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E2

E2
EE

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@
S

S
ER

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SW

SW

SW
N

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EG

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EG

E
PHOTOSENSITIZATIOON
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
A Substance which when added to a reaction mixture
@

@
helps to start the photochemical reaction but itself does
not undergo any chemical change is called photosensitizer
and the process is called photosensitization.
S

S
ER

ER

ER
The photosensitizer simply acts as a carrier of energy
SW

SW

SW
N

N
A

»D
EG

EG

EG

D
hv

E
+
7R

7R

7R
01

01

01
E2

E2

E2
+ A*
EE

EE

EE
D+A D
@

D Donor A = Acceptor
S

S
ER

ER

ER

40
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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E2

E2

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EE

EE

EE
PHOTOCHEMICAL MECHANISMS IN PHOTOSENSITIZATION
@

@
B. POUYET and R. CHAPELON

Laboratoire de Photochimie Appliquée. Université claude

Bernard, Lyon I, 43, Bd du 1i novembre 1918.
F-69622 Villeurbanne Cedex, France
S

S
ER

ER

ER
SW

SW

SW
Abstract -
N

N
Action of light in chemical transformations can be classified in two main groups
A

A
EG

EG

EG
-
Direct photochemical reactions :molecules which absorb lightare that which are

E
transformed.
7R

7R

7R
Photosensitized reactions the light is absorbed by a different molecule to
01

01

01
that we wish to transform.
E2

E2

E2
which absorbs a photon may
EE

EE

EE
In the second case the sensitizer react in two ways
@

@
. Electron transfer.
Energy transfer.
So for photo-oxi dations it is possible to speak about two types :

Type I photo-oxidations: there is either hydrogen atom abstraction, or electron

transfer.
Type II photo-oxidations : energy transfer occurs between excited sensitizer
S

S
ER

ER

ER
and oxy9en giving excited singlet Oxygen; it is a very reactive species.
SW

SW

SW
Rose Bengal, Acridin Orange, Methylene Blue, Chlorophy11 and Hematoporphyrin are
the most current sensitizers. It is Hematoporphyrin that is employed in phototherapy
N

N
in consideration of the two properties
A

is a good sensitizer withoutcells

EG

EG

EG

it important toxicity

E
its Tife time in carcinogenic is longer than in normal cells.
7R

7R

7R
action of light on Hematoporphyrin in i11 cells gives singlet oxygen (strong
01

01

01
The
oxidant) which destroys them. An example of photochemica T studies usefulness is
E2

E2

E2
given.
EE

EE

EE
@

Light can bring about or initiate some chemical reactions, but it is necessary
that one of the constituants in the reactant media absorbs this light.
Then we can have two cases
S

1- The 1ight is absorbed: by the studied reactant which is transformed or reacts

ER

ER

ER

following this absorption it is named a direct photochemical reaction.

SW

SW

SW

ex: thymine dimerization

N

N
A

CH
EG

EG

EG

HN CHa HINT
E

hy

o
7R

7R

7R

260 gm
0
01

01

01
E2

E2

E2
EE

EE

EE
@

Article published online by EDP Sciences and available at http://dx.doi.org/10.1051/jphyscol:1987755

S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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E2

E2

E2
C7-248 JOURNAL DE PHY SIQUE

EE

EE

EE
2-The 1ight is absorbed by a constituant which does not generally participate
@

@
in thereaction: it is only present to catch a photon and then to initiate the che-
mical process. It plays as a kind of "catalyst".
It makes the reaction sensitive to the 1ight: this type of situation is cal1led a
photosensitized reaction.
ex :photosynthesis_and_chlorophy11
S

S
ER

ER

ER
6 CO,+ visible light 02
6 H,0 C6 H12
66
SW

SW

SW
(chtorophyTT)
N

N
To understand the route of a photochemical reaction, it is necessary to give a
A

A
brief simplified scheme of what happens in a molecule which absorbs a photoon.
and
EG

EG

EG
The ground state is the stable state in which the molecules are generally present.

E
For organic molecules this state is a singlet state: that means that spins of elec-
7R

7R

7R
trons in the high energy orbital that is occupied are paired.
01

01

01
The energy of the absorbed photon is used to energize an electron and cause it to
E2

E2

E2
jump to a higher energy level. Two excited electronic states can be obtained. In one,
EE

EE

EE
electron is not changed: this state is termed an excited singlet
the spinIn of thesecond
state. the case, the electron spin is changed and the two electron spins
@

@
are now unpaired giving an excited triplet state.
After photoexcitation, the motecule can folow different paths, according to the
following state energy diagram (1)
S

S
ER

ER

ER
SW

SW

1 SW
N

N
A

A
EG

EG

EG

S k$T

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

iii
@
S

S
ER

ER

ER
SW

SW

SW

In the case of a photosensitized reaction, the photosensitizer can fol1ow two paths
giving:
N

N
A

either, an electron transfer

EG

EG

EG

or, an energy transfer

E
7R

7R

7R

For example, in photo-oxidation with oxygen, it is possible to have

01

01

01

A
I
Type photo-oxidation reactions : the photosensitizer
or
transfers an electron
to the substrate, abstracts an hydrogen atom
E2

E2

E2
EE

EE

EE

S+h +$* (singlet or triplet)

@

S+RH SH+R
R
or st+R' S+ then radicals react with oxygen
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

SW

SW

SW

Common to all branches

N

N
A

A
G

G
 SW

SW

SW
N

N
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C7-249

E2

E2

E2
EE

EE

EE
B Type_II_photo-oxidation reactions the photosensitizer transfers its energy
@

@
to a molecule of oxygen.
+ S (triplet)
s+O2 S+0
oxygen in ground state is in a triplet state contrarily to organic molecules. In the
excited state, obtained by energy transfer, the Oxygen molecule is in a singlet
S

S
state.
ER

ER

ER
let oxygen has special physical properties which allow characterization of it.
Moreover it is a very reactive species It is a strong oxidizing agent.
SW

SW

SW
Among the main photosensitizers Currently used, there are Rose Bengal, Acridin
N

N
Orange, Methylene Blue, Chlorophyl1 and Hematoporphyrin.
A

A
In the phototherapy treatment it is Hematoporphyrin and its derivatives which are
EG

EG

EG
emp1oyed, on account of the three fol lowing properties (2).

E
It is a good sensitizer and the quantum yield of singlet oxygen production
7R

7R

7R
1
is about 0.6.
01

01

01
2 The 1ife time in carcinogenic cells is 1onger than in norma1 cel1s.
E2

E2

E2
3-It has no toxicity for human organi sm.
EE

EE

EE
With Hema toprophyrin (HP) the scheme of action is like type II photo-oxidation (3).
@

@
HP+ hv-HP-.HP*
SHP+0, HP
0
The stages shown being very simplified and schematic.
Thus singlet oxygen hence produced in tumoral cells, destroys them (4).
authorS, that type I photo-oxidaton does not occur
S

S
It has been shown by different
ER

ER

ER
with Hematoporphyrin and it should be noted that generally is derivatives it
off
Hematoporphyrin which are used (see conference of Dr. BRAULT) (5) (6). This is due
SW

SW

SW
to the difference of the penetration of light into cells and also a better efficien-
cy of singlet oxygen production.
N

N
Moreover, the agregate state of molecules, which seems to be an important factor.
A

A
EG

EG

EG

is different in HP and HP derivatives.

E
An absorption spectrum of Hema toporphyrin is given here. Hematoporphyrin derivati-
7R

7R

7R
ves have similar spectra.
The first treatments used white 1ight sources, like xenon 1amps. More recent1y the
01

01

01
use of lasers allows transportation of 1ight along an optical fiber and selective
E2

E2

E2
irradiation of the tumoral ites (7) (8).
EE

EE

EE
Thewave1ength of 630 nm is used and is produced by a dye laser this light has
penetration into the tissues because they have a "window" of absorption
@

@
a good
between 630 and 900 nm.

Optical Density
S

025
ER

ER

ER

02
SW

SW

SW

,.15
N

N
A

g1
EG

EG

EG

E
7R

7R

7R

O L a(nm)
01

01

01

530 560 690 620

E2

E2

E2
EE

EE

EE

Absorption spectrum of H.P. derivatives

@

@
S

S
ER

ER

ER

CY6151 - ENGINEERING CHEMISTRY - I

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E2

E2

E2
EE

EE

EE
(Arbitrary Unlte)

@
S

S
ER

ER

ER
SW

SW

SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
EE

EE

EE
@

@
825 650 665 585 600 620

Quantum yield of *0, production

The destruction of these cells by this technique could be effective up to 20 mm depth.

Unfortunately the light at 630 nm is only sligthly absorbed by H.P. derivatives and
S

S
the problem is to find a new molecule
. are which ..
has a good absorption between 630 nm and
ER

ER

ER
900 nm. Phtalocyanin, chlorine the products towards which research is now
SW

SW

SW
heading (see conf. of Dr. BRAULT).
Of course the true efficiency is found by using "in vivo" experiments, but the
N

N
knowledge of photochemical1 behaviors is important to optimize the treatment condi-
A

tions. For example, to avoid or to minimize the risk of erythema it is necessary to

EG

EG

EG

E
7R

7R

7R
E (rbitrary untt)
01

01

01
E2

E2

E2
3500
EE

EE

EE
@

@
3000

.
2500

2000
S

S
ER

ER

ER

1500
SW

SW

SW
N

N
A

1000
EG

EG

EG

.
E

.
7R

7R

7R

400
01

01

01
E2

E2

E2

A(nm}
EE

EE

EE

00
@

Photochemical effect efficiency

A Rabbit liver
B
Rabbit muscle
S

S
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E2

E2

E2
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@

@
S

S
ER

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SW

SW

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C7-251
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employ the smal1est quantitjes of H.P. derivatives.

E
A photochemica1 study of
0 production indicates that the quantum yield varies
7R

7R

7R
with the wavelength of irradiätion. Taking into account the absorption of tissues and
01

01

01
H.P. derivatives, it is seen that the efficiency also varies wi th wavelength of irra-
E2

E2

E2
diation.
EE

EE

EE
In the same manner, the penetration of light, is more or less important, according
to_the wavelength used.
@

@
The conclusion is that a compromise has to be found between wavelength and penetra
tion. For example, in the case of superficial tumors it would be better to irradiate
by a 1ight near 530 nm.

E (arbitrary un1ts)
S

S
ER

ER

ER
SW

SW

1500 SW
N

N
A

A
EG

EG

EG

E
7R

7R

7R
01

01

01
E2

E2

E2
1000
EE

EE

EE
@

@
500
S

S
ER

ER

ER
SW

SW

SW

.2 3 44 6 depth (nm)
N

Photochemi cal effect efficiency

A

Wavelength of irradiation
EG

EG

EG

620 nm
E

530 nm
7R

7R

7R
01

01

01
E2

E2

E2
EE

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EE
@

@
S

S
ER

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